Using Natural Cinchona Alkaloids to Promote the Enantioselective Addition of Dialkylzinc to N-Diphenylphosphinylimines†
Hai-Le Zhang
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorChun-Mei Fang
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorXin Li
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorLiu-Zhu Gong
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorAi-Qiao Mi
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorXin Cui
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorYao-Zhong Jiang
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorHai-Le Zhang
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorChun-Mei Fang
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorXin Li
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorLiu-Zhu Gong
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorAi-Qiao Mi
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorXin Cui
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorYao-Zhong Jiang
Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorDedicated to Professor ZHOU Wei-Shan on the occasion of his 80th birthday.
Abstract
Cinchona alkaloids are utilized as chiral ligands to promote the enantioselective addition of dialkylzinc to N-diphenylphosphinylimines affording enantiomerically enriched N-diphenylphosphinylamines in up to 91% ee.
References and notes
- 1(a) Blaser, H. U., Chem. Rev. 1992, 92, 935. (b) Sakthivel, K; Notz, W; Bui, T; Barbas, C. F., III, J. Am. Chem. Soc. 2001, 123, 5260. (c) Cordova, A; Notz, W; Zhong, G; Betancort, J. M.; Barbas, C. F., III, J. Am. Chem. Soc. 2002, 124, 1842. (d) Cordova, A; Watanabe, S; Tanaka, F; Nota, W; Barbas, C. F. D., J. Am. Chem. Soc. 2002, 124, 1866. (e) List, B., J. Am. Chem. Soc. 2002, 124, 5656. (f) Kumaragurubaran, N; Juhl, K; Zhuang, W; Bøgevig, A; Jørgensen, K. A., J. Am. Chem. Soc. 2002, 124, 6254. (g) List, B., J. Am. Chem. Soc. 2000, 722, 9336.
- 2(a) Moser, H; Rihs, G; Sauter, H., Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1982, 37 (4), 451. (b) Bloch, R., Chem. Rev. 1998, 98, 1407. (c) Enders, D; Reinhold, U., Tetrahedron: Asymmetry 1997, 8, 1895. (d) Johansson, A., Contemp. Org. Synth. 1995, 2, 393. (e) Jacques, J; Collet, A; Wilen, S. H. In, Enantiomers, Racemates, and Resolution, John Wiley and Sons, New York, 1981. (f) Whitesell, J. K., Chem. Rev. 1989, 89, 1581.
- 3(a) Burk, M. J.; Wang, Y. M.; Lee, J. R., J. Am. Chem. Soc. 1996, 118, 5142. (b) Burk, M. J.; Casy, G; Johnson, N. B., J. Org. Chem. 1998, 63, 6084. (c) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C., J. Am. Chem. Soc. 1998, 120, 5808. (d) Zhu, G. X.; Zhang, X. M., J. Org. Chem. 1998, 63, 9590. (e) Yan, Y. Y.; Rajan Babu, T. V., Org. Lett. 2000, 2, 4137.
- 4(a) Denmark, S. E.; Nicaise, O. J.-C., J. Chem. Soc., Chem. Commun. 1996, 999. (b) Denmark, S. E.; Nicaise, O. J.-C. In. Comprehensive Asymmetric Catalysis, Eds.: E. N. Jacobsen; A. Pfaltz; H. Yamamoto, Springer-Verlag, Berlin, 1999, p. 923. (c) Kobayashi, S; Ishitani, H., Chem. Rev. 1999, 99, 1069.
- 5(a)
Soai, K;
Hatanaka, T;
Miyazawa, T.,
J. Chem. Soc., Chem. Commun.
1992,
1097.
(b)
Andersson, P. G.;
Guijarro, D;
Tanner, D.,
Synlett
1996,
727.
(c)
Andersson, P. G.;
Guijarro, D;
Tanner, D.,
J. Org. Chem.
1997,
62,
7364.
(d)
Guijarro, D;
Pinho, P;
Andersson, P. G.,
J. Org. Chem.
1998,
63,
2530.
(e)
Brandt, P;
Hedberg, C;
Lawonn, K;
Pinho, P;
Andersson, P. G.,
Chem.-Eur. J.
1999,
5,
1692.
10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO;2-M CAS Web of Science® Google Scholar(f) Jimeno, C; Reddy, K. S.; Sola, L; Moyano, A; Pericas, M. A.; Riera, A., Org. Lett. 2000, 2, 3157. (g) Pinho, P; Andersson, P. G., Tetrahedron 2001, 57, 1615.
- 6(a) Zhang, X.-M.; Gong, L.-Z; Mi, A.-Q; Cui, X; Jiang, Y.-Z; Choi, M. C. K.; Chan, A. S. C., Tetrahedron Lett. 2001, 42, 6369. (b) Zhang, X. M.; Lin, W. Q.; Gong, L. Z.; Mi, A. Q.; Cui, X; Jiang, Y. Z.; Choi, M. C. K.; Chan, A. S. C., Tetrahedron Lett. 2002, 43, 1535. (c) Zhang, H.-L.; Zhang, X.-M; Gong, L.-Z; Mi, A.-Q; Cui, X; Jiang, Y.-Z; Choi, M. C. K.; Chan, A. S. C., Org. Lett. 2002, 4, 1399.
- 7 Krzyzanowska, B; Stec, W. J., Synthesis 1978, 521.
- 8 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M; Saket, B. M., J. Chem. Soc., Chem. Commun. 1985, 582.
- 9 Boyd, D. R.; Malone, J. F.; McGuckin, R. M.; Jennings, W. B.; Rutherford, M; Saket, B. M., J. Chem. Soc., Perkin Trans. 2 1988, 1145.
- 10 Jennings, W. B.; Lovely, C. J., Tetrahedron Lett. 1988, 29, 3725.
- 11 Jennings, W. B.; Lovely, C. J., Tetrahedron 1991, 47, 5561.
- 12 Soai, K; Hatanaka, T; Miyazawa, T., J. Chem. Soc, Chem. Commun. 1992, 1097.
- 13 Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osbom, H. M. I.; Raphy, J; Sweeney, J. B., Chem. Commun. 1996, 2631.
- 14 Hou, X.-L; Yang, X.-F; Dai, L.-X; Chen, X.-F., Chem. Commun. 1998, 747.
- 15 Blaser, H. U.; Jalett, H. P., J. Mol. Catal. 1991, 68, 215.
