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N ‐Heterocyclic‐Carbene‐Catalyzed Stereoselective Annulations: An Efficient Strategy for the Synthesis of Chromeno[4,3‐ b ]pyrrolidine Derivatives
Author(s) -
Qi Jing,
Duan XiaoYong,
Cao LiLi,
Wang WenYing
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500266
Subject(s) - pyrrolidine , chemistry , annulation , carbene , stereocenter , aldimine , catalysis , stereoselectivity , organocatalysis , stereochemistry , organic chemistry , combinatorial chemistry , medicinal chemistry , enantioselective synthesis
An N ‐heterocyclic‐carbene‐catalyzed annulation of alkynyl aldehydes and o ‐hydroxy aromatic aldimines for the construction of chromeno[4,3‐ b ]pyrrolidine derivatives has been developed. This cascade Michael/Mannich/lactonization process constructs three new bonds and three consecutive stereogenic centers in a single step with excellent diastereoselectivity and low catalyst loading.