4.4 Article

Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 9, Pages 1322-1325

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.12.139

Keywords

Chromene; Tandem reaction; Enantioselective; Cinchona alkaloid; Organocatalysis; 1,2-Cyclohexanedione; Benzylidenemalononitrile

Funding

  1. Welch Foundation [AX-1593]
  2. National Institute of General Medical Sciences [1SC1GM082718-01]

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2-Amino-8-oxo-tetrahydro-4H-chromene-3-carbonitriles were synthesized for the first time from a tandem Michael addition-cyclization reaction between cyclohexane-1,2-dione and benzylidenemalononitriles An enantioselective synthesis of these compounds was achieved in moderate ee values (up to 63% ee) by using a cinchona alkaloid-derived thiourea catalyst. (C) 2010 Elsevier Ltd All rights reserved.

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