4.4 Article

Organocatalytic highly enantio selective tandem Michael-Knoevenagel reaction for the synthesis of substituted thiochromanes

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 12, Pages 1899-1902

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.01.113

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Funding

  1. NIGMS NIH HHS [S06 GM008194, S06 GM008194-25S10078] Funding Source: Medline

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Enantioenriched tetrasubstituted thiochromanes have been synthesized using a tandem Michael addition-Knoevenagel reaction between 2-mercaptobenzaldehydes and benzylidenernalonates with a 9-epi-aminoquinine thiourea derivative as the catalyst. Steric and electron effects were found to affect profoundly the enantioselectivity and diastereoselectivity of the reaction. (c) 2008 Elsevier Ltd. All rights reserved.

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