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Synfacts 2009(4): 0448-0448
DOI: 10.1055/s-0028-1088096
DOI: 10.1055/s-0028-1088096
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
A Stereoselective Domino Reaction Leading to a Pyrrolizidine Skeleton
J. Tan, X. Xu, L. Zhang, Z. Li, Q. Liu*
Northeast Normal University, Changchun, P. R. of China
Further Information
Publication History
Publication Date:
23 March 2009 (online)

Significance
Xu, Liu and colleagues report a new transformation of 1,4-dien-3-ones (1), which involves a tandem double Michael reaction followed by an intramolecular cyclization and an acyl migration. This one-pot process gives highly substituted azabicycles 3-5 and creates up to four adjacent stereocenters with complete regio- and diastereoselectivity. Using the achiral base catalyst DBU and thermal conditions, the authors obtained the desired products with good yields and demonstrated a broad substrate scope.