Synthesis of a class of new phosphine-oxazoline ligands and their applications in palladium-catalyzed asymmetric addition of arylboronic acids to isatins

Authors:  Qing Li, Pin Wan, Shouliang Wang, Yue Zhuang, Lanning Li, Yougui Zhou, Yuwei He, Rihui Cao, Liqin Qiu, Zhongyuan Zhou

Abstract:
A class of new phosphine-oxazoline ligands was prepared from commercially available and inexpensive starting materials. As the first example, in situ formed catalysts generated from chiral phosphineoxazolines and Pd(OAc)₂ were successfully applied to the asymmetric addition reactions of arylboronic acids to isatins, and 3-aryl-3-hydroxyoxindoles were obtained in up to 97% yields and good enantioselectivities (up to 88% ee). Up to 98% enantiopurity of the products were obtained after one recrystallization.

Keywords:
Asymmetric synthesis
Phosphine ligands
Oxazoline
Palladium
1,2-Addition

Published in: Applied catalysis A: General  (Volume 458, Pages 1-206, 10 May 2013)

Publisher: Elsevier

ISSN Information: 0926-860X

Synthesis of a class of new phosphine-oxazoline ligands and their applications in palladium-catalyzed asymmetric addition of arylboronic acids to isatins

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