4.4 Article

Highly enantioselective Michael addition of acetone to nitroolefins catalyzed by chiral bifunctional primary amine-thiourea catalysts with acetic acid

Journal

TETRAHEDRON
Volume 65, Issue 27, Pages 5265-5270

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.04.087

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Funding

  1. National Natural Science Foundation of China [20402004, 20772029]
  2. New Century Excellent Talents in University [NCET-07-0286]

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Highly enantioselective Michael reaction of acetone with a variety of nitroolefins catalyzed by N-[(1R,2R)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-)-thiourea (1b) together with acetic acid is described. The Michael addition products were obtained in high yields (76-94%) and Lip to 96% ee. (C) 2009 Elsevier Ltd. All rights reserved.

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