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Synfacts 2008(4): 0381-0381  
DOI: 10.1055/s-2008-1042784
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective [4+3] Cycloadditions

Contributor(s): Mark Lautens, Frédéric Ménard
J. P. Olson, H. M. L. Davies*
The State University of New York, Buffalo, USA
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

A domino cyclopropanation-Cope rearrangement sequence was shown to expand the scope of enantioselective reactions of donor/acceptor carbenoids containing benzofurans as the donor moiety. The formal [4+3] cycloadducts 3 are prepared in good yield and high enantioselectivity from a range of dienes 2 or 4. The benzofuranyl diazoacetates 1 are prepared in two steps from commercially available coumaran-3-ones.