Tetrahedron Letters p. 3791 - 3794 (1996)
Update date:2022-08-11
Topics:
Weissman, Steven A.
Ramachandran, P. Veeraraghavan
A series of chirally modified borohydrides of the type lithium B-iso-2- (alkyl)apopinocampheyl-9-borabicyclo[3.3.1]nonyl hydride (2-4 and 8-9) were prepared to enable a strategic development of chiral reagents for the reduction of straight chain aliphatic ketones. Reagent 8 (alkyl = 2- diethylaminoethyl) reduces 2-octanone in 82% ee, significantly higher than that obtained with NB-Enantride (7) under identical conditions. An improved methodology for these reductions is also described.
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