An improved synthesis of a ketone catalyst for asymmetric epoxidation of olefins

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4963-4965

  Shu, Lianhe ^a   Shen, Yu Mei ^a   Burke, Christopher ^a   Goeddel, David ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC EPOXIDATION;

CATALYSTS; GLUCOSE; OXIDATION; SYNTHESIS (CHEMICAL);

KETONES;

ALKENE DERIVATIVE; GLUCOSE; KETONE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; EPOXIDATION; PURIFICATION; REACTION ANALYSIS; SYNTHESIS;

ALKENES; CATALYSIS; CHEMISTRY, ORGANIC; EPOXY COMPOUNDS; GLUCOSE; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0038277410     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0206770     Document Type: Article

References (54)

1. For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. (d) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
2. For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. (d) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
3. For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. (d) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
4. For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. (d) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
5. For reviews on chiral ketone-catalyzed asymmetric epoxidation, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979.
6. For reviews on chiral ketone-catalyzed asymmetric epoxidation, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979.
7. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
8. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
9. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
10. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
11. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
12. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
13. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
14. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
15. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
16. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
17. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
18. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
19. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
20. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
21. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
22. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
23. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
24. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
25. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
26. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
27. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
28. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
29. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
30. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
31. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
32. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C., M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmety 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s)
33. (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
34. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
35. (c) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
36. (a) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551.
37. (b) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929.
38. (c) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435.
39. 2. For a leading review on amine dealkylations with acyl chlorides, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1.
40. 3, more phosgene was required due to the more rapid decomposition of phosgene by these bases.
41. The reaction mixture became orange and viscous, so it is very important that stirring continue at all times. Also, to prevent decomposition, the bath temperature should not exceed 90 °C.
42. Hodge, J. E.; Fisher, B. E. Methods Carbohydr. Chem. 1963, 2, 99.
43. f of the byproduct is about 0.5.
44. f values of 0.8 and 0.2, respectively. The reaction time for the hydrogenation varies with the activity of the Pd catalyst and stirring. Active catalyst and vigorous stirring usually results in shorter reaction time and better yield. Also, the reaction goes faster if less solvent is used.
45. Phosgene is very toxic and needs to be handled carefully.
46. 3.
47. f is about 0.5 using EtOAc as a solvent, and the starting material stays at the baseline.
48. MeOH is used to hydrolyze the unreacted phosgene and the corresponding chloroformate of compound 6. Methanol should be added very slowly at the beginning via pipet, and the reaction mixture should be vigorously stirred to avoid the build-up of HCl, which will catalyze the hydrolysis of the dimethyl ketal of compound 6 to give the undesired diol instead.
49. f of the ketone is about 0.8, but the hydrate only appears slightly above the starting material at around 0.5. The two can be differentiated by color with p-anisaldehyde stain. The hydrate has a reddish tint, while the starting material appears darker.
50. Excess wash should be avoided to reduce impurities which will affect the following recrystallization.
51. The hydrate can be converted to the ketone by extensive drying under high vacuum line.
52. 2O will make the reaction less clean.
53. f about 0.8 in hexanes-EtOAc (1:1)]. The impurity is removed during the subsequent treatment with hexanes-ether (3:1).
54. To simplify the NMR spectrum, the hydrate can be converted to the ketone by heating the compound under vacuum.