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Direct Synthesis of Chiral Allenoates from the Asymmetric CH Insertion of α‐Diazoesters into Terminal Alkynes
Author(s) -
Tang Yu,
Chen Quangang,
Liu Xiaohua,
Wang Gang,
Lin Lili,
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.201501918
Subject(s) - chemistry , cationic polymerization , yield (engineering) , isomerization , terminal (telecommunication) , optically active , stereochemistry , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , materials science , computer science , metallurgy , telecommunications
Abstract The asymmetric CH 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.

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