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Enantio- and diastereoselective Darzens condensations

Lookup NU author(s): Thierry Achard, Professor Michael North, Francesca Pizzato

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Abstract

A cobalt(salen) complex has been shown to catalyse the asymmetric Darzens condensation between α-haloamides and aldehydes, allowing both the relative and absolute stereochemistry of the epoxy-amide products to be controlled. Under optimal conditions, cis-epoxides can be obtained diastereoselectively with up to 50% enantiomeric excess, whilst by changing the leaving group and base, trans-epoxides can be produced diastereoselectively with up to 43% enantiomeric excess. © 2007 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Achard TJR, Belokon' YN, Ilyin M, Moskalenko M, North M, Pizzato F

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2007

Volume: 48

Issue: 17

Pages: 2965-2969

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tetlet.2007.03.009

DOI: 10.1016/j.tetlet.2007.03.009

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