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Asymmetric Ring‐Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N , N ′‐Dioxide–Scandium(III) Complex
Author(s) -
Xia Yong,
Lin Lili,
Chang Fenzhen,
Fu Xuan,
Liu Xiaohua,
Feng Xiaoming
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.201506909
Subject(s) - nucleophile , scandium , catalysis , alcohol , ring (chemistry) , chemistry , medicinal chemistry , thiol , carboxylic acid , organic chemistry
A highly efficient asymmetric ring‐opening reaction of cyclopropyl ketones with a broad range of thiols, alcohols and carboxylic acids has been first realized by using a chiral N , N ′‐dioxide–scandium(III) complex as catalyst. The corresponding sulfides, ethers, and esters were obtained in up to 99 % yield and 95 % ee . This is also the first example of one catalytic system working for the ring‐opening reaction of donor–acceptor cyclopropanes with three different nucleophiles, let alone in an asymmetric version.