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Synfacts 2007(12): 1313-1313  
DOI: 10.1055/s-2007-991335
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Water-Compatible Iminium Catalysis

Contributor(s): Benjamin List, Subhas Chandra Pan
C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, Á. Puente, S. Vera
Universidad del País Vasco, San SebastiÁn, Spain
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

The authors report organocatalytic asymmetric Michael reactions of different carbon-centered nucleophiles with enals using water as the only solvent. A new family of prolinol-based catalysts has been developed that enable water-compatible iminium catalysis. Catalyst 1 having the dihexyl substituents was found to be the best catalyst when used in combination with benzoic acid as additive. With 5-20 mol% of catalyst 1 good to high enantioselectivities (er = 87:13 to >99:1) are obtained for different carbon-centered nucleophiles.