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Enantioselective Vinylogous Michael/Cyclization Cascade Reaction of Acyclic β,γ‐Unsaturated Amides with Isatylidene Malononitriles: Asymmetric Construction of Spirocyclic Oxindoles
Author(s) -
Li TianZe,
Xie Jin,
Jiang Yu,
Sha Feng,
Wu XinYan
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500469
Subject(s) - chemistry , enantioselective synthesis , michael reaction , cascade , cascade reaction , optically active , pyrimidine , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , chromatography
Abstract The first direct and enantioselective vinylogous Michael/cyclization cascade reaction between acyclic β,γ‐unsaturated amides and isatylidene malononitriles has been developed. Optically active spirocyclic oxindoles have been obtained in good‐to‐excellent yields (84–96%) and enantioselectivity (79–97% ee ) in the presence of 2 mol% (DHQD) 2 PYR [2,5‐diphenyl‐4,6‐bis(9‐ O ‐dihydroquinyl)pyrimidine].