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Palladium‐Catalyzed Domino Process to Spirooxindoles: Ligand Effect on Aminopalladation versus Carbopalladation
Author(s) -
Jaegli Stéphanie,
Erb William,
Retailleau Pascal,
Vors JeanPierre,
Neuville Luc,
Zhu Jieping
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.201000312
Subject(s) - domino , intramolecular force , ligand (biochemistry) , domino effect , palladium , sequence (biology) , catalysis , process (computing) , combinatorial chemistry , chemistry , computer science , stereochemistry , organic chemistry , political science , receptor , programming language , law , biochemistry
Double intra, from linear to spiro : A Pd‐catalyzed domino sequence involving an intramolecular aminopalladation followed by arylation that convert linear anilides 1 into the functionalized spiropyrrolidine‐3,3′‐oxindoles 2 in good to excellent yields is presented. The use of 2‐di‐ tert ‐butylphosphino‐2′‐methylbiphenyl as a ligand determines the success of the domino process. A trans ‐aminopalladation mechanism seems to account for the observed diastereoselectivity.