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Borane-Mediated Aldol Cycloreduction of Monoenone Monoketones: Diastereoselective Formation of Quaternary Centers

Ryan R. Huddleston, David F. Cauble, and Michael J. Krische*

Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712

J. Org. Chem., 2003, 68 (1), pp 11–14

DOI: 10.1021/jo020629f

Publication Date (Web): November 20, 2002

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mkrische@mail.utexas.edu

Abstract

Exposure of monoenone monoketones to catecholborane in THF at ambient temperature results in tandem 1,4-reduction−aldol cyclization. For aromatic and heteroaromatic enones, six-membered cyclic aldol products are formed in excellent yield with high levels of syn diastereoselectivity. Five-membered ring formation proceeds less readily, but the yield of cyclized product is improved through introduction of Rh(I) salts.

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Published In Issue January 10, 2003
Received October 1, 2002

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Article

Borane-Mediated Aldol Cycloreduction of Monoenone Monoketones: Diastereoselective Formation of Quaternary Centers