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Synfacts 2009(11): 1280-1280
DOI: 10.1055/s-0029-1218116
DOI: 10.1055/s-0029-1218116
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Secondary Amine/N-Heterocyclic Carbene Catalyzed Cascade Sequence
S. P. Lathrop, T. Rovis*
Colorado State University, Fort Collins, USA
Further Information
Publication History
Publication Date:
22 October 2009 (online)
Significance
A one-pot, asymmetric multicatalytic formal [3+2] reaction between α,β-unsaturated aldehydes 3 and 1,3-dicarbonyl compounds 4 is described. A combined use of secondary amine catalyst 1 and N-heterocyclic carbene catalyst 2 provides rapid access to functionalized cyclopentanones 5 and bicycles 6 and 7 containing three contiguous stereocenters. Products were obtained in good yields, with high enantioselectivity and moderate diastereoselectivity.