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Ir‐SpinPHOX Catalyzed Enantioselective Hydrogenation of 3‐Ylidenephthalides
Author(s) -
Ge Yao,
Han Zhaobin,
Wang Zheng,
Feng ChenGuo,
Zhao Qian,
Lin GuoQiang,
Ding Kuiling
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807639
Subject(s) - enantioselective synthesis , asymmetric hydrogenation , chemistry , catalysis , oxazoline , enantiomer , phosphine , ligand (biochemistry) , combinatorial chemistry , enantiomeric excess , noyori asymmetric hydrogenation , organic chemistry , stereochemistry , receptor , biochemistry
The first asymmetric hydrogenation of 3‐ylidenephthalides has been developed using the Ir I complex of a spiro[4,4]‐1,6‐nonadiene‐based phosphine‐oxazoline ligand (SpinPHOX) as the catalyst, affording a wide variety of chiral 3‐substituted phthalides in excellent enantiomeric excesses (up to 98 % ee ). The utility of the protocol has been demonstrated in the asymmetric synthesis of chiral drugs NBP and BZP precursor, as well as the natural products chuangxinol and typhaphthalide.