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Synfacts 2005(1): 0140-0140  
DOI: 10.1055/s-2005-872188
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Double C-H Activation of Dihydronaphthalenes

Contributor(s): Mark Lautens, Josephine Yuen
H. M. L. Davies*, Q. Jin
University at Buffalo, The State University of New York, USA
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

A formal C-H activation of 1,2-dihydronaphthalenes was observed using dirhodium tetrakis[(S)-N-dodecylbenzenesulfonyl]prolinate [Rh2(S-DOSP)4] and an excess of methyl vinyldiazoacetates. The postulated mechanism involves a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement. The generation of four new stereocenters occurred with excellent enantio- and diastereoselectivity.