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Synfacts 2005(3): 0317-0317  
DOI: 10.1055/s-2005-921645
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Reductive Aldol Cyclizations: Synthesis of β-Hydroxylactones

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
H. W. Lam*, P. M. Joensuu
University of Edinburgh, UK
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

This paper reports the construction of synthetically useful β-hydroxylactones via reductive aldol cyclizations. Various copper salts, hydride sources and phosphine ligands were screened and Cu(OAc)2, 1,1,3,3-tetramethylhydrosiloxane (TMDS), and (R)-3,5-xyl-MeO-BIPHEP proved to be the optimal reagents, but only modest enantioselectivity was obtained (up to 83% ee). Reasonable yields (60-70%) were attained for the formation of 5- and 6-membered lactones as well as high diastereoselectivity.