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Highly Diastereoselective Sulfonium Ylide Rearrangements to Quaternary Substituted Indolines
Author(s) -
Boyarskikh Vyacheslav,
Nyong Abijah,
Rainier Jon D.
Publication year - 2008
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.200801336
Subject(s) - sulfonium , stereocenter , ylide , chemistry , stereochemistry , quaternary carbon , catalysis , organic chemistry , enantioselective synthesis , salt (chemistry)
Quat. centers : Sulfonium ylide intermediates generated from halogenated vinyl diazoacetates and 2‐thioindoles in the presence of a Rh II complex undergo highly diastereoselective [3,3] rearrangements to indolines having an asymmetric quaternary carbon center with an adjacent halogenated stereocenter (see scheme).