title: Asymmetric Ring-Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N,N'-Dioxide-Scandium(III) Complex.
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.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Yong
authors.initials: Y
authors.lastname: Xia
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Fenzhen
authors.initials: F
authors.lastname: Chang
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Xuan
authors.initials: X
authors.lastname: Fu
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China). liuxh@scu.edu.cn.
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China). xmfeng@scu.edu.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China). xmfeng@scu.edu.cn.|State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China). xmfeng@scu.edu.cn.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
keywords: asymmetric catalysis; cyclopropyl ketones; nucleophiles; ring opening; scandium catalysts