Chiral boron catalysts for reduction of ketones and process for

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

1991-07-15

1993-02-23

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

Patent

active

051891778

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.

REFERENCES:
Enders et al., Org. Synth., Col. vol. 6, 642-549.
Corey et al., J. Amer. Chem. Soc., 1987, 109, 7925-7926.
Kapfhammer et al., Hoppe-Seyler Zeit. Physiol Chem. 1933.233 43-52.
Corey et al., J. Org. Chem. 1988, 53, 2861-2863.
Corey et al., J. Amer. Chem. Soc. 1987 109, 5551-5553.
Enders et al., Bull. Soc. Chem Belg., 1988, 97, 691-704.
Corey et al., Tet. Letters, 1989, 30 6375-6278.
Mathre et al. J. Org. Chem. 56, 751-762 (1991).

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