A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6576-6582

  Chan, Wing Kei ^a   Yu, Wing Yiu ^a   Che, Chi Ming ^a   Wong, Man Kin ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVITY;

NUCLEAR MAGNETIC RESONANCE; OXIDATION; TITRATION;

ESTERS;

ACETONITRILE; ALKENE; BETA CYCLODEXTRIN; ESTER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; NAPHTHALENE DERIVATIVE; STILBENE; STYRENE DERIVATIVE; TERPINEOL;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; COVALENT BOND; ENANTIOSELECTIVITY; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TITRIMETRY;

BINDING SITES; CARBOHYDRATE SEQUENCE; CYCLODEXTRINS; KETONES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; STEREOISOMERISM; TERPENES;

EID: 0042009333     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034296d     Document Type: Article

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24. For excellent reviews on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979. For references on asymmetric epoxidation catalyzed by chiral binap ketones, see: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) 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. (f) Yang, D.; Jiao, G.-S.; Yip, Y.-C.; Lai, T.-H.; Wong, M.-K. J. Org. Chem. 2001, 66, 4619.
25. For excellent reviews on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979. For references on asymmetric epoxidation catalyzed by chiral binap ketones, see: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) 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. (f) Yang, D.; Jiao, G.-S.; Yip, Y.-C.; Lai, T.-H.; Wong, M.-K. J. Org. Chem. 2001, 66, 4619.
26. For excellent reviews on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979. For references on asymmetric epoxidation catalyzed by chiral binap ketones, see: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) 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. (f) Yang, D.; Jiao, G.-S.; Yip, Y.-C.; Lai, T.-H.; Wong, M.-K. J. Org. Chem. 2001, 66, 4619.
27. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
28. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
29. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
30. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
31. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
32. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
33. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
34. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
35. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
36. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
37. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
38. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
39. For selected references on asymmetric epoxidation mediated by chiral dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (c) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (d) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (e) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (f) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8622. (g) Armstrong, A.; Hayter, B. R. J. Chem. Soc., Chem. Commun. 1998, 621. (h) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (i) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (j) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (k) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929. (l) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (m) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943.
40. (a) Deary, M. E.; Davies, D. M. Carbohydr. Res. 1998, 309, 17.
41. (b) Deary, M. E.; Davies, D. M. Carbohydr. Res. 1999, 317, 10.
42. Yang, D.; Wong, M.-K.; Wang, X.-C.; Tang, Y.-C. J. Am. Chem. Soc. 1998, 120, 6611.
43. (a) Botsi, A.; Yannakopoulou, K.; Perly, B.; Hadjoudis, E. J. Org. Chem. 1995, 60, 4017.
44. (b) Salvatierra, D.; Jaime, C.; Virgili, A.; Sanchez-Ferrando, F. J. Org. Chem. 1996, 61, 9578.
45. (c) Botsi, A.; Perly, B.; Hadjoudis, E. J. Chem. Soc., Perkin Trans. 2 1997, 89.
46. (d) Salvatierra, D.; Sanchez-Ruiz, X.; Garduno, R.; Cervello, E.; Jaime, C.; Virgili, A.; Sanchez-Ferrando, F. Tetrahedron 2000, 56, 3035.
47. (e) Zubiaur, M.; Jaime, C. J. Org. Chem. 2000, 65, 8139.
48. For a reference regarding the use of dimethyldioxirane for limonene epoxidation, see: Asouti, A.; Hadjiarapoglou, L. P. Synlett 2001, 12, 1847.
49. For references regarding the use of CDs as chiral templates for asymmetric epoxidation, see: (a) Banfi, S.; Colonna, S.; Julia, S. Synth. Commun. 1983, 13, 1049. (b) Hu, Y.; Harada, A.; Takahashi, S. Synth. Commun. 1988, 18, 1607. (c) Colonna, S.; Manfredi, A.; Annunziata, R.; Gaggero, N.; Casella, L. J. Org. Chem. 1990, 55, 5862. (d) Sakuraba, H.; Tanaka, Y. Org. Prep. Proced. Int. 1998, 30, 226.
50. For references regarding the use of CDs as chiral templates for asymmetric epoxidation, see: (a) Banfi, S.; Colonna, S.; Julia, S. Synth. Commun. 1983, 13, 1049. (b) Hu, Y.; Harada, A.; Takahashi, S. Synth. Commun. 1988, 18, 1607. (c) Colonna, S.; Manfredi, A.; Annunziata, R.; Gaggero, N.; Casella, L. J. Org. Chem. 1990, 55, 5862. (d) Sakuraba, H.; Tanaka, Y. Org. Prep. Proced. Int. 1998, 30, 226.
51. For references regarding the use of CDs as chiral templates for asymmetric epoxidation, see: (a) Banfi, S.; Colonna, S.; Julia, S. Synth. Commun. 1983, 13, 1049. (b) Hu, Y.; Harada, A.; Takahashi, S. Synth. Commun. 1988, 18, 1607. (c) Colonna, S.; Manfredi, A.; Annunziata, R.; Gaggero, N.; Casella, L. J. Org. Chem. 1990, 55, 5862. (d) Sakuraba, H.; Tanaka, Y. Org. Prep. Proced. Int. 1998, 30, 226.
52. For references regarding the use of CDs as chiral templates for asymmetric epoxidation, see: (a) Banfi, S.; Colonna, S.; Julia, S. Synth. Commun. 1983, 13, 1049. (b) Hu, Y.; Harada, A.; Takahashi, S. Synth. Commun. 1988, 18, 1607. (c) Colonna, S.; Manfredi, A.; Annunziata, R.; Gaggero, N.; Casella, L. J. Org. Chem. 1990, 55, 5862. (d) Sakuraba, H.; Tanaka, Y. Org. Prep. Proced. Int. 1998, 30, 226.
53. 1H NMR spectroscopy. The chemical shift of the methyl group protons (δ ∼2.4) of the ketone form is about 0.9 ppm downfield shift compared with that of the hydrate form (δ ∼1.5) (see: Pocker Y.; Meany J. E.; Zadoroj, C. J. Phys. Chem. 1971, 75, 792). In this work, compared with the literature data, the singlet at δ 2.45 was assigned to be the methyl group protons of the ketone form of 2 while the singlet at δ 1.54 was assigned to be the methyl group protons of the hydrate form of 2.