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Synthesis of Chiral Aminocyclopropanes by Rare‐Earth‐Metal‐Catalyzed Cyclopropene Hydroamination
Author(s) -
Teng HuaiLong,
Luo Yong,
Wang Baoli,
Zhang Liang,
Nishiura Masayoshi,
Hou Zhaomin
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609853
Subject(s) - hydroamination , enantioselective synthesis , chemistry , cyclopropene , stereoselectivity , catalysis , combinatorial chemistry , metal , intermolecular force , organic chemistry , molecule
The search for efficient and selective routes for the synthesis of chiral aminocyclopropane derivatives is of great interest and importance as these structures are important components of biologically active natural products and pharmaceuticals. We herein report the enantioselective intermolecular hydroamination of substituted cyclopropenes with various amines catalyzed by chiral half‐sandwich rare‐earth‐metal complexes. This method constitutes a 100 % atom‐efficient route for the synthesis of a variety of chiral α‐aminocyclopropane derivatives in high yields (up to 96 %) and excellent stereoselectivity (up to >20:1 d.r. and 99 % ee ) under mild reaction conditions (25 °C).