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Switchable Access to Different Spirocyclopentane Oxindoles by N‐Heterocyclic Carbene Catalyzed Reactions of Isatin‐Derived Enals and N‐Sulfonyl Ketimines
Author(s) -
Wang Lei,
Li Sun,
Blümel Marcus,
Puttreddy Rakesh,
Peuronen Anssi,
Rissanen Kari,
Enders Dieter
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.201704210
Subject(s) - stereocenter , isatin , annulation , moiety , catalysis , carbene , chemistry , sulfonyl , combinatorial chemistry , quaternary carbon , organic chemistry , enantioselective synthesis , alkyl
A novel NHC‐catalyzed annulation protocol for the asymmetric synthesis of biologically important β‐lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin‐derived enals, and N‐sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates.