Chiral ligands derived from Abrine. 3. Asymmetric Pictet-Spengler reaction of Abrine methyl ester and synthesis of chiral 1,2,3,4-tetrahydro-β-carbolines as promoters in addition of diethylzinc toward aromatic aldehydes

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5971-5974

  Dai, Wei Min ^a   Zhu, Hua Jie ^a   Hao, Xiao Jiang ^b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; LIGAND; N METHYLTRYPTOPHAN; OXAZOLIDINE DERIVATIVE; TRYPTOLINE DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030581372     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01290-7     Document Type: Article

References (41)

1. 1. Pictet-Spengler reaction, see: Mundy, B. P.; Ellerd, M. G. Name Reactions and Reagents in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1988, p 164.
2. 2. "Isoquinolines" in The Chemistry of Heterocyclic Compounds Greth, G., Ed.; Wiley: New York, 1981, Part I, vol 38.
3. 3. (a) Yoneda, N. Chem. Pharm. Bull. 1965, 13, 1231-1240.
4. (b) Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089-1119.
5. (c) Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Wu, G. S.; Yamanaka, E.; Hutchins, L.; DiPierro, M.; Cook, J. M. J. Org. Chem. 1979, 44, 535-545.
6. (d) Shimizu, M.; Ishikawa, M.; Komoda, Y.; Nakajima, T.; Yamaguchi, K.; Sakai, S. Chem. Pharm. Bull. 1984, 32, 1313-1325.
7. (e) Zhang, L. H.; Cook, J. M. Heterocycles 1988, 27, 1357-1363, and 2795-2802.
8. (f) Sandrin, J.; Hollinshead, S. P.; Cook, J. M. J. Org. Chem. 1989, 54, 5636-5640.
9. (g) Narayanan, K.; Cook, J. M. J. Org. Chem. 1991, 56, 5733-5736.
10. (h) Fu, X.; Cook, J. M. J. Am. Chem. Soc. 1992, 114, 6910-6912.
11. (i) Bi, Y.; Zhang, L.-H.; Hamaker, L. K.; Cook, J. M. J. Am. Chem. Soc. 1994, 116, 9027-9041.
12. (j) Martin, S. F.; Clark, C. W.; Corbett, J. W. J Org. Chem. 1995, 60, 3236-3242.
13. 4. (a) Ungemach, F.; DiPierro, M.; Weber, R.; Cook, J. M. J. Org. Chem. 1981, 46, 164-168.
14. (b) Jawdosiuk, M.; Cook, J. M. J. Org. Chem. 1984, 49, 2699-2701.
15. (c) Zhang, L.-H.; Bi, Y.-Z.; Yu, F.-X.; Menzia, G.; Cook, J. M. Heterocycles 1992, 34, 517-547.
16. (d) Czerwinski, K. M.; Deng, L.; Cook, J. M. Tetrahedron Lett. 1992, 33, 4721-4724.
17. (e) Zhang, P.; Cook, J. M. Tetrahedron Lett. 1995, 36, 6999-7002.
18. Also see: (f) Bailey, P. D.; Collier, I. D.; Hollinshead, S. P.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. J. Chem. Soc., Chem. Commun. 1994, 1559-1560.
19. (g) De la Figuera, N.; Alkorta, I.; García-López, M. T.; Herranz, R.; González-Muñiz, R. Tetrahedron 1995, 51, 7841-7856.
20. 5. (a) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron 1994, 50, 11865-11884.
21. (b) Soe, T.; Kawate, T.; Fukui, N.; Nakagawa, M. Tetrahedron Lett. 1995, 36, 1857-1860.
22. 6. Abrine was isolated from the seeds of Abrus precatorius collected in Yunnan Province of China. Dictionary of Organic Compounds, 5th ed.; Buckingham, J. Ed.; Champman and Hall: New York, 1982; p 4084.
23. 7. (a) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron Asymm. 1995, 6, 1857-1860.
24. (b) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron Asymm. 1996, 7, 1245-1248.
25. 13C NMR and HRMS.
26. 9. (a) Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
27. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
28. (c) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
29. For reviews, see: (d) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
30. (e) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
31. (f) Oguni, N. Kikan Kagaku Sosetsu 1993, No. 19, 143-154.
32. 10. (a) Soai, K.; Watanabe, M. Tetrahedron Asymm. 1991, 2, 97-100.
33. (b) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. J. Org. Chem. 1991, 56, 2218-2224.
34. 11. Selected recent examples: pyridines, see: a) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc. Chem. Commun. 1990, 982-983.
35. (b) Ishizaki, M.; Hoshino, O. Tetrahedron Asymm. 1994, 5, 1901-1904.
36. (c) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191-1203.
37. Pyrimidines. see: (c) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature, 1995, 378, 767-768.
38. (d) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471-472.
39. Quinolines, see: (e) Collomb, P.; von Zelewsky, A. Tetrahedron Asymm. 1995, 6, 2903-2904.
40. Pyrazoles and imidazoles, see: (f) Kotsuki, H.; Hayakawa, H.; Wakao, M.; Shimanouchi, T.; Ochi, M. Tetrahedron Asymm. 1995, 6, 2665-2668.
41. Oxazolines, see: (g) Alien, J. V.; Williams, J. M. J. Tetrahedron Asymm. 1994, 5, 277-282.