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Catalytic Double Stereoinduction in Asymmetric Allylic Alkylation of Oxindoles
Author(s) -
Trost Barry M.,
Zhang Yong
Publication year - 2010
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.200902770
Subject(s) - stereocenter , tsuji–trost reaction , enantioselective synthesis , nucleophile , allylic rearrangement , chemistry , steric effects , alkylation , catalysis , stereochemistry , vicinal , combinatorial chemistry , organic chemistry
A highly regio‐, diastereo‐, and enantioselective allylic alkylation reaction of 3‐monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric variations of the nucleophile. The use of appropriate N‐protecting group is particularly important for achieving high regio‐ and diastereoselectivity. Products from this reaction, containing vicinal quaternary‐tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis.