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Cu I ‐Catalysed Enantioselective Alkyl 1,4‐Additions to ( E )‐Nitroalkenes and Cyclic Enones with Phosphino‐Oxazoline Ligands
Author(s) -
Shin Minkyeong,
Gu Minji,
Lim Sung Soo,
Kim MinJae,
Lee JuHyung,
Jin HyeongGyu,
Jang Yun Hee,
Jung Byunghyuck
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800476
Subject(s) - chemistry , oxazoline , enantioselective synthesis , stereoselectivity , alkyl , conjugate , catalysis , yield (engineering) , medicinal chemistry , stereochemistry , organic chemistry , mathematical analysis , materials science , mathematics , metallurgy
Catalytic enantioselective conjugate additions of simple alkyl groups to nitroalkenes or cyclic enones that result in the formation of tertiary C–C bonds are described. For these stereoselective addition reactions, new chiral phosphino‐oxazoline ligands were synthesized and used. The reactions were promoted by a Cu‐based catalyst (2 mol‐%), and gave the chiral products in up to 92 % yield with 95 % ee . A larger‐scale synthesis was demonstrated, and the origin of the stereoselectivity was proposed based on DFT calculations.