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Synfacts 2006(1): 0034-0034  
DOI: 10.1055/s-2005-921676
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Dynamic Kinetic Resolution in Cu-Catalyzed Conjugate Hydride Addition

Contributor(s): Mark Lautens, Y. Eric Fang
M. P. Rainka, J. E. Milne, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

A dynamic kinetic resolution (DKR) of α,β-unsaturated lactones via a Cu-catalyzed conjugate hydride addition was reported. This highly efficient approach afforded excellent yields and good ee’s in the formation of β,γ-disubstituted γ-lactones from racemic starting materials. The methodology was demonstrated in an extremely concise enantioselective total synthesis of Eupomatilone-3, which was achieved in six steps and 48% overall yield.