Journal
TETRAHEDRON-ASYMMETRY
Volume 12, Issue 13, Pages 1907-1912Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(01)00333-0
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A series of chiral bifunctional squaric prolinol ligands, having N, S substituents at C(3) of the squaric ring were synthesized and applied to the asymmetric borane reduction of prochiral ketones via an in situ formed chiral boron heterocycle, affording secondary alcohols with high yields and excellent enantiomeric excesses (up to 99%). The crystal structure of 5a was obtained and the mechanism of the catalytic asymmetric reduction is also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
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