Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations
Reddi, Rambabu N.
Chi, Yonggui Robin
Date of Issue2017
School of Physical and Mathematical Sciences
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.
Angewandte Chemie International Edition
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Angewandte Chemie International Edition, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/anie.201700045].