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Construction of Fused Pyrrolidines and β‐Lactones by Carbene‐Catalyzed C−N, C−C, and C−O Bond Formations
Author(s) -
Wu Xingxing,
Hao Lin,
Zhang Yuexia,
Rakesh Maiti,
Reddi Rambabu N.,
Yang Song,
Song BaoAn,
Chi Yonggui Robin
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700045
Subject(s) - carbene , chemistry , heteroatom , catalysis , pyrrolidine , intermolecular force , molecule , organocatalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , ring (chemistry)
A carbene‐catalyzed intermolecular C−N bond formation, which initiates a highly selective cascade reaction for the synthesis of pyrrolidine fused β‐lactones, is disclosed. The nitrogen‐containing bicyclic β‐lactone products are obtained with good yields and excellent stereoselectivities. Synthetic transformations of the reaction products into useful functional molecules, such as amino catalysts, can be efficiently realized under mild reaction conditions. Mechanistically, this study provides insights into modulating the reactivities of heteroatoms, such as nitrogen atoms, in challenging carbene‐catalyzed asymmetric carbon–heteroatom bond‐forming reactions.