Synfacts 2009(4): 0448-0448  
DOI: 10.1055/s-0028-1088096
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

A Stereoselective Domino Reaction Leading to a Pyrrolizidine Skeleton

Contributor(s): Benjamin List, Olga Lifchits
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.