Tetrahedron Letters p. 6275 - 6278 (1989)
Update date:2022-08-04
Topics:
Corey, E. J.
Link, John O.
An efficient synthesis of (S)-(-)-2-(di-β-naphthylhydroxymethyl)pyrrolidine (1) makes available the oxazaborolidine derivates 2 and 3 which are excellent catalysts for borane reduction of a variety of achiral ketones to chiral secondary alcohols, e.g. acetophenone, 98percent ee; α-tetralone, 95percent ee; and methyl-4-oxo-4-phenyl butyrate, 96percent ee.The synthesis of chiral 1-deuterio primary alcohols from achiral aldehydes with B-n-butyloxazaborolidine (4) as catalyst in the presence of 2H-catecholborane as reductant has also been demonstrated, e.g. benzaldehyde, 95percent ee; cyclohexanecarboxaldehyde, 92percent ee; and n-octanal, 90percent ee.
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