Issue 2, 2014

Diastereoselective synthesis of epoxide-fused benzoquinolizidine derivatives using intramolecular domino aza-Michael addition/Darzens reaction

Abstract

An efficient and diastereoselective strategy based on an intramolecular domino aza-Michael/Darzens reaction to synthesize epoxide-fused benzoquinolizidines has been described. Three bonds (1 C–C, 1 C–N and 1 C–O), three rings and three chiral centers can be constructed in a single pot under very mild conditions. All the products were isolated in only one diastereomer with 40–80% yields.

Graphical abstract: Diastereoselective synthesis of epoxide-fused benzoquinolizidine derivatives using intramolecular domino aza-Michael addition/Darzens reaction

Supplementary files

Article information

Article type
Communication
Submitted
16 Oct 2013
Accepted
30 Oct 2013
First published
30 Oct 2013

Org. Biomol. Chem., 2014,12, 265-268

Diastereoselective synthesis of epoxide-fused benzoquinolizidine derivatives using intramolecular domino aza-Michael addition/Darzens reaction

J. Guo, X. Sun and S. Yu, Org. Biomol. Chem., 2014, 12, 265 DOI: 10.1039/C3OB42068J

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