Enantiospecific synthesis of pyridinylmethyl pyrrolidinemethanols and catalytic asymmetric borane reduction of prochiral ketones

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 177-182

  Zhang, Yong Xin ^a   Du, Da Ming ^a   Chen, Xiao ^a   Lü, Shao Feng ^a   Hua, Wen Ting ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 (DIPHENYLMETHANOL) 1 (2 PYRIDYLMETHYL)PYRROLIDINE; BORANE DERIVATIVE; KETONE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE; PROLINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0346787836     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.037     Document Type: Article

References (22)

1. (a) Deloux L., Srebnik M. Chem. Rev. 93:1993;763-784;
2. (b) Corey E.J., Helal C.J. Angew. Chem., Int. Ed. Engl. 37:1998;1986-2012;
3. (c) Schunicht C., Biffis A., Wulff G. Tetrahedron. 56:2000;6041.
4. (a) Togni A., Venanzi L.M. Angew. Chem., Int. Ed. Engl. 33:1994;497-526 (b) Larsen R.D., Corley E.G., King A.O., Carroll J.D., Davis P., Verhoeven T.R., Reider P.J., Labelle M., Gauthier J.Y., Xiang Y.B., Zamboni R.J. J. Org. Chem. 61:1996;3398-3405 (c) Ponzo V.L., Kaufman T.S. Tetrahedron Lett. 36:1995;9105-9108.
5. Itsuno S., Ito K., Hirao A., Nakahama S. J. Chem. Soc., Chem. Commun. 1983;469-470.
6. Corey E.J., Bakshi R.K., Shibata S. J. Am. Chem. Soc. 109:1987;5551-5553.
7. (a) Molvinger K., Lopez M., Court J. Tetrahedron: Asymmetry. 11:2000;2263-2266 (b) Ma M.F.P., Li K.Y., Zhou Z.H., Tang C.C., Chan A.S.C. Tetrahedron: Asymmetry. 10:1999;3259-3261 (c) Sato S., Watanabe H., Asami M. Tetrahedron: Asymmetry. 11:2000;4329-4340 (d) Santhi V., Rao J.M. Tetrahedron: Asymmetry. 11:2000;3553-3560 (e) Brunin T., Cabou J., Bastin S., Brocard J., Pélinski L. Tetrahedron: Asymmetry. 13:2002;1241-1243.
8. Yang G.S., Hu J.B., Zhao G., Ding Y., Tnag M.H. Tetrahedron: Asymmetry. 10:1999;4307-4311.
9. (a) Hu J.B., Zhao G., Yang G.S., Ding Z.D. J. Org. Chem. 66:2001;303-304 (b) Hu J.B., Zhao G., Ding Z.D. Angew. Chem., Int. Ed. 40:2001;1109-1111.
10. (a) Li K.Y., Zhou Z.H., Wang L.X., Chen Q.F., Zhao G.F., Zhou Q.L., Tang C.C. Tetrahedron: Asymmetry. 14:2003;95-100 (b) Gamble M.P., Smith A.R., Wills M. J. Org. Chem. 63:1998;6068-6071.
11. (a) Zhou H.B., Lü S.M., Xie R.G., Chan A.S.C., Yang T.K. Tetrahedron Lett. 42:2001;1107-1110;
12. (b) Zhang J., Zhou H.B., Liu S.M., Luo M.M., Xie R.G., Choi M.C.K., Zhou Z.Y., Chan A.S.C., Yang T.K. Tetrahedron: Asymmetry. 12:2001;1907-1912.
13. (a) O'Neil I.A., Turner C.D., Kalindjian S.B. Synlett. 1997;777-778;
14. (b) Shen Y.C., Feng X.M., Zhang G.L., Jiang Y.Z. Synlett. 2002;1353-1355.
15. Chen X., Du D.M., Hua W.T. Tetrahedron: Asymmetry. 14:2003;999-1007.
16. This compound has been synthesized using an alternative procedure: Chelucci G., Falorni M., Glacomelli G. Tetrahedron: Asymmetry. 1:1990;843-849.
17. Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255-2260.
18. (a) Itsuno S., Nakano M., Miyazaki K., Masuda H., Ito K. J. Chem. Soc., Chem. Commun. 1985;2039-2044 (b) Chen C.P., Prasad K., Repic O. Tetrahedron Lett. 32:1991;7175-7178 (c) Mathie D.J., Thompson A.S., Douglas A.W., Hoogsteen K., Carroll J.D., Corley E.G., Grabowski E.J.J. J. Org. Chem. 58:1993;2880-2888.
19. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-215883. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
20. Corey E.J., Shibata S., Bakshi R.K. J. Org. Chem. 53:1988;2861-2863.
21. Sheldrick, G. M. SHELXS-97. Program for the Solution of Crystal Structures, University of Goettingen, Germany, 1997.
22. Sheldrick, G. M. SHELXL-97. Program for the Refinement of Crystal Structure, University of Goettingen, Germany, 1997.