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Design, Synthesis, and Application of a Chiral Sulfinamide Phosphine Catalyst for the Enantioselective Intramolecular Rauhut–Currier Reaction
Author(s) -
Su Xiao,
Zhou Wei,
Li Yangyan,
Zhang Junliang
Publication year - 2015
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.201500907
Subject(s) - enantioselective synthesis , intramolecular force , kinetic resolution , phosphine , catalysis , phos , chemistry , combinatorial chemistry , organic chemistry , biochemistry
Abstract A novel class of chiral sulfinamide phosphine catalysts (Xiao‐Phos) are reported, which can be easily prepared from inexpensive commercially available starting materials. The Xiao‐Phos catalysts showed good performance in enantioselective intramolecular Rauhut–Currier reactions, generating α‐methylene‐γ‐butyrolactones in high yields with up to 99 % ee under mild conditions. Moreover, kinetic resolution and parallel kinetic resolution were also observed with the use of two different substituted racemic precursors.