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'On Water' Iminium/Enamine Catalysis: Organocatalytic Enantioselective Cyclopropanation of α,β-Unsaturated Aldehydes

Uxue Uria, Jose L. Vicario*, Dolores Badía, Luisa Carrillo, Efraim Reyes, Amaia Pesquera

*Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain, Email:

U. Uria, J. L. Vicario, D. Badía, L. Carrillo, E. Reyes, A. Pesquera, Synthesis, 2010, 701-713.

DOI: 10.1055/s-0029-1218645


Use of water as reaction medium for O-TMS-diarylprolinol-catalyzed cyclopropanation reactions of α,β-unsaturated aldehydes with diethyl bromomalonate enables a base-free reaction system. A modified O-TMS-diarylprolinol incorporating a hydrophobic alkyl side chain has been identified as a promising catalyst for this reaction.

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Key Words

Cyclopropanes, Organocatalysis, Green Chemistry, Domino Reaction, Michael Addition, ‘On Water'

ID: J66-Y2010-0530