title: Direct Synthesis of Chiral Allenoates from the Asymmetric C-H Insertion of α-Diazoesters into Terminal Alkynes.
abstract: The asymmetric C-H insertion of α-diazoesters into 1-alkynes was achieved using chiral cationic guanidinium salts and copper(I) complexes. Optically active 2,4-disubstituted allenoates were generated under mild reaction conditions from various α-diazoesters and 1-alkynes in high yield (up to 99%) and enantioselectivity (up to 97:3 e.r.). Control experiments excluded the possibility of an asymmetric isomerization of alkynoates.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Quangang
authors.initials: Q
authors.lastname: Chen
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China). liuxh@scu.edu.cn, xmfeng@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).
authors.forename: Gang
authors.initials: G
authors.lastname: Wang
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).|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China).
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
keywords: allenes; asymmetric catalysis; copper; diazo compounds; synthetic methods