Asymmetric Ring‐Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N, N′‐Dioxide–Scandium(III) Complex. (23rd September 2015)

• Record Type: Journal Article
• Authors: Xia, Yong; Lin, Lili; Chang, Fenzhen; Fu, Xuan; Liu, Xiaohua; Feng, Xiaoming
• Is Part Of: Angewandte Chemie. Volume 127:Number 46(2015)
• Page Start: 13952
• Page End: 13956
• Publication Date: 2015-09-23
• Subjects: Asymmetrische Katalyse -- Cyclopropylketone -- Nucleophile -- Ringöffnung -- Scandium‐Katalysatoren; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201506909
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.