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Palladium‐Catalyzed Asymmetric Allylation of Prochiral Nucleophiles: Synthesis of 3‐Allyl‐3‐Aryl Oxindoles
Author(s) -
Trost Barry M.,
Frederiksen Mathias U.
Publication year - 2004
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.200460335
Subject(s) - aryl , tsuji–trost reaction , nucleophile , catalysis , palladium , allylic rearrangement , chemistry , transformation (genetics) , combinatorial chemistry , alkyl , organic chemistry , biochemistry , gene
Excellent yields and enantioselectivies are attained in the synthesis of 3‐alkyl‐3‐aryl oxindoles based on the Pd‐catalyzed asymmetric allylic alkylation (AAA) reaction. This approach utilizes a nonbasic hydroxylic additive in the transformation of 3‐aryl oxindoles into complex, synthetically valuable oxindoles (see scheme).