Process for preparing enantiomerically pure diarylprolinols

Details Process for preparing enantiomerically pure diarylprolinols Process for preparing enantiomerically pure diarylprolinols

1995-05-04

1996-06-18

Brust, Joseph Paul

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20708

Patent

active

055279236

ABSTRACT:
The present invention relates to a new process for preparing enantiomerically pure diarylprolinols, especially (R)-(+)- or (S)-(-)-2-(diphenylhydroxymethyl)-pyrrolidine (R)-(+)- or (S)-(-)-.alpha.,.alpha.-diphenyl-(2-pyrrolidinyl)-methanol) starting from proline.

REFERENCES:
patent: 5039802 (1991-08-01), Blacklock et al.
"The First Enantioselective Total Syntheses of the Allopumiliotoxin A Alkaloids 267A and 339B", Goldstein et al., J. Org. Chem., 1992, vol. 57, pp. 1179-1190.
"Highly Enantioselective Borane Reduction of Ketones Catalyzed by Chiral Oxazaborolidines, Mechanism and Synthetic Implications" -E. J. Corey et al., J. Am. Chem. Soc., 1987, vol. 109, pp. 5551-5553.
"Synthesis of (S)-(-)alpha, alpha-Diphenyl-2-pyrrolidinemethanol", Y. Liao-Chemical Abstracts, vol. 119, No. 11, 13-Sep. 1993; C.A.: 117057j.
"Convenient Method for the Synthesis of Chiral .alpha.,.alpha.-Diphenyl-2-pyrrolidinylmethanol"-J. V. Bhaskar Kanth et al., Tetrahedron, vol. 49, No. 23, 1993, pp. 5127-5132.
"A Practical Enantioselective Synthesis of .alpha.,.alpha.-Diaryl-2-pyrrolidinemethanol. Preparation and Chemistry of the Corresponding Oxazaborolidines"-D. J. Mathre et al., J. Org. Chem., 1991, vol. 56, pp. 751-762.
"Large Scale Preparation of Versatile Chiral Auxiliaries Derived from (S)-Proline" -D. Enders et al., Bull. Soc. Chim. Belg., vol. 97, No. 8-9, 1988, pp. 691-704.

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