4.4 Article

Asymmetric Michael addition of glycine imines via quaternary ammonium ion catalysis

Journal

TETRAHEDRON LETTERS
Volume 46, Issue 26, Pages 4461-4464

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.04.096

Keywords

phase-transfer catalysis; Michael addition; amino acids

Funding

  1. Engineering and Physical Sciences Research Council [GR/S86129/01] Funding Source: researchfish

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The asymmetric Michael addition of glycine imine esters to simple alpha, beta-unsaturated ketones via PTC is investigated. It is found that by employing 1 mol % of a chiral quaternary ammonium salt, derived from alpha-methylnaphthylamine in conjunction with CS2CO3, high enantioselectivities can be obtained in conjugate additions involving simple alkylvinylketones. (c) 2005 Elsevier Ltd. All rights reserved.

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