Synfacts 2009(12): 1399-1399  
DOI: 10.1055/s-0029-1218211
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Intramolecular Michael Addition of a Nitroalkane into a Conjugated Ester

Contributor(s): Benjamin List, Olga Lifchits
W. J. Nodes, D. R. Nutt, A. M. Chippindale, A. J. A. Cobb*
University of Reading, UK
Further Information

Publication History

Publication Date:
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.