Premium
Enantioselective Cycloadditions of Vinyl Cyclopropanes and Nitroolefins for Functionally and Optically Enriched Nitrocyclopentanes
Author(s) -
Li WenKe,
Liu ZeShui,
He Long,
Kang TaiRan,
Liu QuanZhong
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402219
Subject(s) - diastereomer , enantioselective synthesis , chemistry , cyclopropane , cycloaddition , yield (engineering) , organic chemistry , optically active , catalysis , combinatorial chemistry , stereochemistry , ring (chemistry) , materials science , metallurgy
Palladium‐catalyzed enantioselective cycloaddition of vinyl cyclopropane dicarbonitriles and nitroolefins was achieved to generate structurally and optically enriched nitrocyclopentanes with three consecutive chiral carbon centers in up to 96 % yield and with up to 92 % ee . The two diastereoisomers produced in each reaction are readily separable by simple chromatography. The present method allows the preparation of both diastereoisomers in optically enriched form.