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Synlett 2003(12): 1934-1936  
DOI: 10.1055/s-2003-41458
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© Georg Thieme Verlag Stuttgart · New York

Effect of the Michael Acceptor in the Asymmetric Intramolecular Stetter Reaction

Mark S. Kerr, Tomislav Rovis*
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA
Fax: +1(970)4911801; e-Mail: rovis@lamar.colostate.edu;
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Publication History

Received 20 June 2003
Publication Date:
19 September 2003 (online)

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Abstract

The effect of different Michael acceptors was evaluated in the catalytic asymmetric intramolecular Stetter reaction. Utilizing a readily prepared chiral triazolium salt as a nucleophilic carbene precursor, the reactivity and selectivity of substrates containing different electron-deficient double bonds was shown to vary significantly under identical reaction conditions.

Keywords

nucleophilic carbenes - catalytic asymmetric Stetter - Michael acceptors - umpolung chemistry

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