Enantioselective allylation of nitro group-stabilized carbanions catalyzed by chiral crown ether phosphine-palladium complexes

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9090-9096

  Sawamura, Masaya ^a   Nakayama, Yuki ^b   Tang, Wen Ming ^b,c   Ito, Yoshihiko ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c Guizhou Teachers University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001384844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961343b     Document Type: Article

References (54)

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8. Exceptionally high selectivities have been reported in the enantioselective allylation of 2-cyanopropionate promoted by a palladium-rhodium two-component catalyst system: Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
9. Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 2586.
10. 1H NMR analysis with a chiral shift reagent, was confirmed to be correct by GLC analysis with Chiraldex G-TA (120 °C, base-line separation). Separation of the allylation product of 2-methyl-1-phenylbutane-1,3-dione by chiral GLC was not successful.
11. For a review, see: Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
12. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
13. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
14. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
15. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
16. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
17. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
18. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
19. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
20. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
21. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
22. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
23. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
24. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
25. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
26. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
27. For recent papers in accord with this concept, see: (a) Sawamura, M.; Kitayama, K.; Ito, Y. Tetrahedron: Asymmetry 1993, 4, 1829. (b) Ward, J.; Börner, A.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 849. (c) Börner, A.; Holz, J.; Kless, A.; Heller, D.; Berens, U. Tetrahedron Lett. 1994, 35, 6071. (d) Börner, A.; Ward, J.; Ruth, W.; Holz, J.; Kless, A.; Heller, D.; Kagan, H. B. Tetrahedron. 1994, 50, 10419. (e) Holz, J.; Börner, A.; Kless, A.; Borns, S.; Trinkhaus, S.; Selke, R.; Heller, D. Tetrahedron: Asymmetry 1995, 6, 1973. (f) Börner, A.; Kless, A.; Kempe, R.; Heller, D.; Holz, J.; Baumann, W. Chem. Ber. 1995, 128, 767. (g) Börner, A.; Holz, J.; Ward, J.; Kagan, H. B. J. Org. Chem. 1993, 58, 6814. (h) Börner, A.; Kless, A., Holz, J.; Baumann, W.; Tillack, A.; Kadyrov, R. J. Organomet. Chem. 1995, 490, 213. (i) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 4601. (j) Fields, L. B.; Jacobsen, E. N. Tetrahedron: Asymmetry 1993, 4, 2229. (k) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. (l) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (m) Spencer, J.; Gramlich, V.; Häusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41. (n) MacFarland, D. K.; Landis, C. R. Organometallics 1996, 15, 483. (o) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194. (p) Kimmich, B. F. M.; Landis, C. R.; Powell, D. R. Organometallics 1996, 15, 4141.
28. For the palladium-catalyzed allylic alkylations of nitro group-stabilized carbanions, see the following. For α-nitro ketones: (a) Ognyanov, V.; Hesse, M. Synthesis 1985, 645. For α-nitro esters: (b) Genet, J. P.; Ferroud, D. Tetrahedron Lett. 1984, 25, 3579. (c) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. (d) Lalonde, J. J.; Bergbreiter, D. E.; Wong, C.-H. J. Org. Chem. 1988, 53, 2323. For nitroalkanes: (e) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523. (f) Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
29. For the palladium-catalyzed allylic alkylations of nitro group-stabilized carbanions, see the following. For α-nitro ketones: (a) Ognyanov, V.; Hesse, M. Synthesis 1985, 645. For α-nitro esters: (b) Genet, J. P.; Ferroud, D. Tetrahedron Lett. 1984, 25, 3579. (c) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. (d) Lalonde, J. J.; Bergbreiter, D. E.; Wong, C.-H. J. Org. Chem. 1988, 53, 2323. For nitroalkanes: (e) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523. (f) Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
30. For the palladium-catalyzed allylic alkylations of nitro group-stabilized carbanions, see the following. For α-nitro ketones: (a) Ognyanov, V.; Hesse, M. Synthesis 1985, 645. For α-nitro esters: (b) Genet, J. P.; Ferroud, D. Tetrahedron Lett. 1984, 25, 3579. (c) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. (d) Lalonde, J. J.; Bergbreiter, D. E.; Wong, C.-H. J. Org. Chem. 1988, 53, 2323. For nitroalkanes: (e) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523. (f) Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
31. For the palladium-catalyzed allylic alkylations of nitro group-stabilized carbanions, see the following. For α-nitro ketones: (a) Ognyanov, V.; Hesse, M. Synthesis 1985, 645. For α-nitro esters: (b) Genet, J. P.; Ferroud, D. Tetrahedron Lett. 1984, 25, 3579. (c) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. (d) Lalonde, J. J.; Bergbreiter, D. E.; Wong, C.-H. J. Org. Chem. 1988, 53, 2323. For nitroalkanes: (e) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523. (f) Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
32. For the palladium-catalyzed allylic alkylations of nitro group-stabilized carbanions, see the following. For α-nitro ketones: (a) Ognyanov, V.; Hesse, M. Synthesis 1985, 645. For α-nitro esters: (b) Genet, J. P.; Ferroud, D. Tetrahedron Lett. 1984, 25, 3579. (c) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. (d) Lalonde, J. J.; Bergbreiter, D. E.; Wong, C.-H. J. Org. Chem. 1988, 53, 2323. For nitroalkanes: (e) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523. (f) Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
33. For the palladium-catalyzed allylic alkylations of nitro group-stabilized carbanions, see the following. For α-nitro ketones: (a) Ognyanov, V.; Hesse, M. Synthesis 1985, 645. For α-nitro esters: (b) Genet, J. P.; Ferroud, D. Tetrahedron Lett. 1984, 25, 3579. (c) Genet, J. P.; Grisoni, S. Tetrahedron Lett. 1986, 27, 4165. (d) Lalonde, J. J.; Bergbreiter, D. E.; Wong, C.-H. J. Org. Chem. 1988, 53, 2323. For nitroalkanes: (e) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523. (f) Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck, J. E., II; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616.
34. For the use of 2-nitropropionates for the preparation of α-methylated α-amino acids, see: Robinson, B.; Shepherd, D. M. J. Chem. Soc. 1961, 5037. See also ref 7d.
35. (a) Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138.
36. (b) Hayashi, T.; Yamazaki, A. J. Organomet. Chem. 1981, 413, 295.
37. (R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl: Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
38. (S,S)-1,2-Bis(diphenylphosphino)butane: Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.
39. (S,S)-2,3-0-Isapropylidene-2,3-dihydroxy-1,4-bis(diphenylphoaphino) butane: Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
40. Fujimoto, R. A.; Boxer, J.; Jackson, R. H.; Simke, J. P.; Neale, R. F.; Snowhill, E. W.; Barbaz, B. J.; Williams, M.; Sills, M. A. J. Med. Chem. 1989, 32, 1259.
41. The ee was not further improved by lowering the reaction temperature to -50 °C; 7 days, 77% yield, 79% ee.
42. 4 was observed in the enantioselective allylation of nitro ketone 3a.
43. For the synthesis and biological activity of optically active α-alkylated amino acids, see: Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405 and references cited therein.
44. (a) Izumi, Y.; Tatsumi, S.; Imaida, M.; Fukuda, Y.; Akabori, S. Bull. Chem. Soc. Jpn. 1965, 38, 1338.
45. (b) Abei, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507.
46. (c) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918.
47. Ram, S.; Ehrenkaufer, R. E. Synthesis 1986, 133.
48. For other examples of proposed ternary complexes involving crown ether, metal cation, and enolate anion, see: (a) Cram, D. J.; Sogah, D. Y. J. Chem. Soc., Chem. Commun. 1981, 625. (b) De Vries, E. F. J.; Ploeg, L.; Colao, M.; Brussee, J.; Van der Gen, A. Tetrahedron: Asymmetry 1995, 6, 1123.
49. For other examples of proposed ternary complexes involving crown ether, metal cation, and enolate anion, see: (a) Cram, D. J.; Sogah, D. Y. J. Chem. Soc., Chem. Commun. 1981, 625. (b) De Vries, E. F. J.; Ploeg, L.; Colao, M.; Brussee, J.; Van der Gen, A. Tetrahedron: Asymmetry 1995, 6, 1123.
50. (a) Fischer, R. H.; Weitz, H. M. Synthesis 1980, 261.
51. (b) Bischoff, C.; Schröder, E. J. Prakt. Chem. 1972, 314, 891.
52. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
53. Bailey, W. J.; Madoff, M. J. Am. Chem. Soc. 1954, 76, 2707.
54. Kornblum, N.; Blackwood, R. K. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. 4, p 454.