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Highly Enantio‐ and Diastereoselective Generation of Two Quaternary Centers in Spirocyclopropanation of Oxindole Derivatives.
Author(s) -
Noole Artur,
Sucman Natalia S.,
Kabeshov Mikhail A.,
Kanger Tõnis,
Macaev Fliur Z.,
Malkov Andrei V.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203099
Subject(s) - oxindole , cyclopropanation , yield (engineering) , cascade , quaternary , chemistry , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , materials science , biology , paleontology , chromatography , metallurgy
Spirocyclopropanes : Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2‐chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high yield and high enantio‐ and diastereoselectivity (see scheme).