Tetrahedron Asymmetry p. 433 - 436 (1990)
Update date:2022-08-24
Topics:
Ramachandran, P. Veeraraghavan
Brown, Herbert C.
Swaminathan, Shankar
Lithium B-iso-2-ethylapopinocampheyl-9-borabicyclo<3.3.1>nonyl hydride (Eapine-Hydride), prepared by hydroboration of 2-ethylapopinene with 9-borabicyclo<3.3.1>nonane, followed by treatment with tert-butyllithium, is as effective as NB-Enantride for the chiral reduction of prochiral ketones.For example Eapine-Hydride reduces 2-octanone, 3-methyl-2-butanone, and acetylcyclohexane in 77percent (75percent, 79percent), 77percent (68percent), and 80percent (80percent) ee, respectively, at -100 deg C. (Values in parenthesis are for NB-Enantride).
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