Chiral catalysts for reduction of ketones and process for their

Details Chiral catalysts for reduction of ketones and process for their Chiral catalysts for reduction of ketones and process for their

1992-10-26

1993-11-23

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 13, C07F 502, C07B 4900, C07B 4100, C07D21122

Patent

active

052645851

ABSTRACT:
The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl- methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of diborane, borane-dimethyl sulfide or borane-tetrahydrofuran reductions of ketones to secondary alcohols.

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Corey et al, Tet. Letters, 30, 6375-6378 (1989).
Mathre et al, J. Org. Chem., 56, 751-762 (1991).
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