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Synthesis of Cyclopropane Spirooxindoles by means of a Vinylogous Organocatalytic Cascade
Author(s) -
César da Silva Rodrigo,
Chatterjee Indranil,
EscuderoAdán Eduardo,
Weber Paixão Marcio,
Melchiorre Paolo
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400014
Subject(s) - chemistry , cyclopropane , iminium , stereoselectivity , cascade , tandem , selectivity , cascade reaction , sequence (biology) , organocatalysis , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , ion , catalysis , ring (chemistry) , biochemistry , materials science , chromatography , composite material
The stereoselective construction of spirooxindolic cyclopropane derivatives is achieved by means of a vinylogous cascade reaction that successfully integrates a vinylogous iminium ion/dienamine tandem sequence. The chemistry capitalizes upon a rare example of asymmetric 1,6‐addition to 2,4‐dienals, which proceeds with exclusive δ‐site selectivity.