4.4 Article

Stereoselective preparation of chiral compounds in Mannich-type reactions of a bicyclic imine and phenols or indole

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 49, Pages 6619-6622

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.10.081

Keywords

Mannich reaction; Betti reaction; Bicyclic imines; Stereoselectivity

Funding

  1. Polish Ministry of Science and Higher Education for the Faculty of Chemistry of the Wroclaw University of Technology

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Mannich-type reactions of a chiral bicyclic imine and various nucleophiles yield the corresponding adducts with good to high diastereoselectivity. The influence of the reaction conditions on the yield and stereochemical outcome is investigated. The configuration of the products is established by H-1 NMR spectroscopy, and the major isomers of two adducts are characterized by X-ray crystallography. (C) 2014 Elsevier Ltd. All rights reserved.

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