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Synfacts 2010(11): 1253-1253  
DOI: 10.1055/s-0030-1258792
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Copper-Catalyzed Boration

Contributor(s): Mark Lautens, Norman Nicolaus
I.-H. Chen, M. Kanai*, M. Shibasaki*
Institute of Microbial Chemistry, Tokyo and The University of Tokyo, Japan
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

A copper(I)-catalyzed conjugated enantioselective boration of β,β-disubstituted linear enones 1 is described. Bis(pinacolato)diboron (2) was used as the borylation reagent and it was found that secondary 1,2-diphenylethylendiamine ligands give the best yields and the highest enantioselecti­vities. Furthermore, it was possible to oxidize the enantiomerically enriched boration products into the corresponding cross aldol-type products (3 → 4) without racemization and in excellent yield.