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Synfacts 2007(3): 0315-0315  
DOI: 10.1055/s-2007-968234
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Rauhut-Currier Reactions Promoted by Protected Cysteine

Contributor(s): Benjamin List, Subhas Chandra Pan
C. E. Aroyan, S. J. Miller*
Boston College, Chestnut Hill, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Here the authors report the first enantioselective intramolecular Rauhut-Currier cyclization reaction. Cysteine-derived catalyst 1 in combination with t-BuOK (6 equiv) and water (20 equiv) has been found to be effective for the reaction. With 20 mol% or 100 mol% of catalyst 1, moderate to good yields (41-75%) and high enantio­selectivities (er = 84:16 to 97.5:2.5) are obtained for different aryl- or alkyl-substituted bis(enone)s.