Enantioselective allylzincation of cyclic aldimines in the presence of anionic bis-oxazoline ligand

Journal of the American Chemical Society

Volumn 118, Issue 35, 1996, Pages 8489-8490

  Nakamura, Masaharu ^a   Hirai, Atsushi ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029812556     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961213k     Document Type: Article

References (29)

1. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
2. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
3. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
4. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
5. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
6. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
7. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
8. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
9. Review: (a) Volkmann, R. A. In Comprehensive Organic Synthesis, Additions to C-X π-Bonds; Schreiber, S. L. Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12. (b) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Additions to N-silyl imines: (c) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341. Watanabe, K.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 1531. Addition to N-phosphinoyl imines: (d) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097. Additions to N-acyl imines: (e) Katrizky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437. Additions to nitrones: (f) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313. Additions to E-aldimines: (g) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429 and references cited therein. (h) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
10. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
11. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
12. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
13. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
14. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
15. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
16. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Helmchen, G.; Krotz, A.; Ganz, K. T.; Hansen, D. Synlett 1991, 257. Hall, J.; Lehn, J.-M.; DeCian, A.; Fischer, J. Helv. Chim. Acta 1991, 74, 1. Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
17. 2-Zn (40% recovery), which can be quantitatively converted to 3 without racemization (cf. ref 3).
18. We speculate that the lower ee is due to a competing nonselective pathway. Note that, in the reaction of 3 with cyclopropenone acetals (ref 3), the ligand with R = t-Bu gave higher enantioselectivity than those with R = i-Pr and Ph.
19. Mann, J. In Natural Products; Longman Scientific & Technical: Harlow, 1994; Chapter 7.
20. The reaction of benzyl Grignard and benzylzinc reagents in the presence of 2 (R = i-Pr) showed poor enantioselectivity.
21. (a) Grisar, J. M.; Claxton, G. P.; Stewart, K. T. Synthesis 1974, 284.
22. (b) Poisel, H. Monatsh. Chem. 1978, 109, 925.
23. (c) Scully, F. E., Jr. J. Org. Chem. 1980, 45, 1515.
24. Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656. Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121 and references cited therein.
25. Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656. Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121 and references cited therein.
26. Meyers, A. I.; Dickman, D. A.; Boes, M. Tetrahedron 1987, 43, 5095.
27. Kawate, T.; Yamada, H.; Soe, T.; Nakagawa, M. Tetrahedron: Asymmetry 1996, 7, 1249. We thank Prof. M. Nakagawa for provision of experimental data before publication.
28. Ukaji, Y.; Tsukamoto, K.; Nasada, Y.; Shimizu, M.; Fujisawa, T. Chem. Lett. 1993, 221.
29. Aketa, K.-I.; Terashima, S.; Yamada, S.-I. Chem. Pharm. Bull. 1976, 24, 621.