Palladium‐Catalyzed Domino Process to Spirooxindoles: Ligand Effect on Aminopalladation versus Carbopalladation | Zendy

Jaegli Stéphanie | Zendy; Erb William | Zendy; Retailleau Pascal | Zendy; Vors JeanPierre | Zendy; Neuville Luc | Zendy; Zhu Jieping | Zendy

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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.

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