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… - Organic & …, 2019 - pubs.rsc.org
Y Wang, Y Chen, X Li, Y Mao, W Chen, R Zhan, H Huang
Organic & Biomolecular Chemistry, 2019pubs.rsc.org
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.
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.
The Royal Society of Chemistry
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