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Enantioselective Aza‐Ene‐type Reactions of Enamides with Gold Carbenes Generated from α‐Diazoesters
Author(s) -
Zhao Feng,
Li Nan,
Zhang Tao,
Han ZhiYong,
Luo ShiWei,
Gong LiuZhu
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612208
Subject(s) - chemistry , reactivity (psychology) , yield (engineering) , enantioselective synthesis , catalysis , ene reaction , medicinal chemistry , brønsted–lowry acid–base theory , decomposition , combinatorial chemistry , stereochemistry , organic chemistry , medicine , materials science , alternative medicine , pathology , metallurgy
Carbophilic gold carbenes generated from the decomposition of α‐diazoesters show high reactivity towards enamides, leading to an unprecedented aza‐ene‐type reaction. The presence of 0.1 mol % of a chiral Brønsted acid co‐catalyst is sufficient to give synthetically relevant γ‐keto esters in excellent yields and selectivities (up to 99 % yield, 97 % ee ).