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Palladium‐Catalyzed Asymmetric Allylic Alkylation of 3‐Aryloxindoles with Allylidene Dipivalate: A Useful Enol Pivalate Product
Author(s) -
Trost Barry M.,
Masters James T.,
Burns Aaron C.
Publication year - 2013
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.201209783
Subject(s) - enol , tsuji–trost reaction , nucleophile , catalysis , palladium , alkylation , yield (engineering) , allylic rearrangement , chemistry , organic chemistry , materials science , metallurgy
Triple A : The catalytic asymmetric allylic alkylation (AAA) of 3‐aryloxindoles with allylidene dipivalate is described. This reaction affords stable, synthetically useful enol pivalates in high yield and with excellent regio‐ and enantioselectivity. A broad range of substrates is tolerated, including unprotected and 3‐heteroaryl nucleophiles.