Issue 16, 2019

Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

Abstract

An enantioselective [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones has been successfully developed through a squaramide catalysis strategy. This protocol provides an efficient and mild access to obtain pyrano[2,3-c]pyrrole scaffolds containing contiguous quaternary and tertiary stereogenic centers in excellent yields (up to 99%) with high levels of diastereo- and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the observed stereoselectivity.

Graphical abstract: Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

Supplementary files

Article information

Article type
Paper
Submitted
20 Feb 2019
Accepted
26 Mar 2019
First published
26 Mar 2019

Org. Biomol. Chem., 2019,17, 3945-3950

Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

Y. Wang, Y. Chen, X. Li, Y. Mao, W. Chen, R. Zhan and H. Huang, Org. Biomol. Chem., 2019, 17, 3945 DOI: 10.1039/C9OB00419J

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