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Catalytic Asymmetric β,γ Activation of α,β‐Unsaturated γ‐Butyrolactams: Direct Approach to β,γ‐Functionalized Dihydropyranopyrrolidin‐2‐ones
Author(s) -
Jiang Xianxing,
Liu Luping,
Zhang Panpan,
Zhong Yuan,
Wang Rui
Publication year - 2013
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.201302622
Subject(s) - enantioselective synthesis , closet , annulation , computer science , process (computing) , catalysis , chemistry , combinatorial chemistry , organic chemistry , engineering , programming language , civil engineering
Skeleton in the closet : The title reaction enables the development of the first catalytic β,γ‐selective Diels–Alder [4+2] annulation of α,β‐unsaturated γ‐butyrolactams (see scheme; Boc= tert ‐butoxycarbonyl, Ts=4‐toluenesulfonyl). This process provides a direct method for the enantioselective construction of bi‐ or tricyclic dihydropyranopyrrolidin‐2‐one skeletons in only one step.