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Enantioselective Synthesis of Sterically Hindered Tertiary α‐Aryl Oxindoles via Palladium‐Catalyzed Decarboxylative Protonation. An Experimental and Theoretical Mechanistic Investigation
Author(s) -
Biosca Maria,
Jackson Mark,
Magre Marc,
Pàmies Oscar,
Norrby PerOla,
Diéguez Montserrat,
Guiry Patrick J.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800507
Subject(s) - chemistry , enantioselective synthesis , protonation , steric effects , palladium , aryl , catalysis , combinatorial chemistry , organic chemistry , ion , alkyl
Abstract We have developed the first catalytic asymmetric preparation of sterically hindered tertiary α‐aryl oxindoles via enantioselective palladium‐catalyzed decarboxylative protonation of the corresponding α‐aryl‐β‐amido allyl esters. The reaction occurs under very mild conditions and in short reaction times, providing excellent yields and promising enantioselectivities (ee's up to 78%). We have also performed an experimental investigation of the reaction mechanism and employed theoretical calculations to understand the nature of the enantioselectivity‐determining step.