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Asymmetric Yttrium‐Catalyzed C(sp 3 )−H Addition of 2‐Methyl Azaarenes to Cyclopropenes
Author(s) -
Luo Yong,
Teng HuaiLong,
Nishiura Masayoshi,
Hou Zhaomin
Publication year - 2017
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.201705431
Subject(s) - yttrium , enantioselective synthesis , cyclopropane , catalysis , norbornane , chemistry , medicinal chemistry , carbon fibers , organic chemistry , ring (chemistry) , materials science , oxide , composite number , composite material
An enantioselective C−H addition to a C=C bond represents the most atom‐efficient route for the construction of chiral carbon–carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium‐catalyzed C(sp 3 )−H bond addition of 2‐methyl azaarenes, such as 2‐methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl‐functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee ).
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