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Synfacts 2009(9): 1032-1032  
DOI: 10.1055/s-0029-1217786
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

One-Step Synthesis of Furofuranes

Contributor(s): Benjamin List, Corinna Reisinger
E. Reyes, G. Talavera, J. L. Vicario, D. Badía, L. Carrillo
Universidad del País Vasco/Euskal Herriko Unibertsitatea, Bilbao, Spain
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

A secondary amine catalyzed asymmetric domino reaction between dihydroxyacetone dimer (2) and α,β-unsaturated aldehydes 1 is described which furnishes hexahydrofuro[3,4-c]furanes 3 in good to excellent yields along with high diastereo- and enantioselectivities in a single step. The title oxa-Michael-aldol-hemiacetalization sequence comprises the consecutive formation of two C-O and one C-C bond and the generation of four stereocenters.