Method for the in situ preparation of chiral compounds...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S405000

Reexamination Certificate

active

10574871

ABSTRACT:
A process for the in situ preparation of chiral compounds derived from oxazaborolidine-borane complexes, wherein a metal borohydride, a Lewis base and an inorganic acid ester are brought together and an optically active amino alcohol and optionally a halide are then added. The compound obtained is a complex that is useful as a catalyst in asymmetric reduction reactions. The reaction is performed by adding the substance to be reduced, particularly prochiral ketones or ether oximes, in order to synthesize chiral alcohols or chiral amines.

REFERENCES:
patent: 5189177 (1993-02-01), Blacklock et al.
patent: 5264574 (1993-11-01), Carroll et al.
patent: 94/26751 (1994-11-01), None
Abiko et al. “An Improved, Convenient Procedure for Reduction of Amino Acids to Aminoalcohols: Use of NaBH4-H2SO4” Tetrahedron Letters vol. 33, No. 38 p. 5517-5518.
Bell et al. “The Reduction of Organic Halogen Compounds by Sodium Borohydride” The Journal of Organic Chemistry, vol. 34 No. 12 Dec. 1969 p. 3923-3926.
Periasmy “New Organic Synthetic Methods Using the NaBH4/I2System” ACS Symposium Series, 2001, 783 p. 65-78.

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