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Asymmetric Conjugate Alkynylation of Cyclic α,β‐Unsaturated Carbonyl Compounds with a Chiral Diene Rhodium Catalyst
Author(s) -
Dou Xiaowei,
Huang Yinhua,
Hayashi Tamio
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509778
Subject(s) - diene , chemistry , conjugate , rhodium , catalysis , reagent , medicinal chemistry , alkyne , ligand (biochemistry) , alkynylation , organic chemistry , mathematical analysis , biochemistry , natural rubber , receptor , mathematics
Asymmetric conjugate alkynylation of cyclic α,β‐unsaturated carbonyl compounds (ketones, esters, and amides) was realized by use of diphenyl[(triisopropylsilyl)ethynyl]methanol as an alkynylating reagent in the presence of a rhodium catalyst coordinated with a new chiral diene ligand (Fc‐bod; bod=bicyclo[2.2.2]octa‐2,5‐diene, Fc=ferrocenyl) to give high yields of the corresponding β‐alkynyl‐substituted carbonyl compounds with 95–98 % ee .