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Efficient Intramolecular Michael Addition of a Nitroalkane into a Conjugated Ester
W. J. Nodes, D. R. Nutt, A. M. Chippindale, A. J. A. Cobb*
University of Reading, UK
20 November 2009 (online)
Cobb and colleagues report an intramolecular Michael addition of nitro-substituted α,β-unsaturated esters 1, leading to cyclized products 3 with up to three contiguous stereocenters. The products were obtained in generally good yields and diastereoselectivities and with invariably excellent enantioselectivity, albeit only after seven days. They could be further elaborated to biologically important γ-amino acid precursors 4 in two to three steps.