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Highly Enantioselective Michael Addition of Malonates to β‐CF 3 ‐β‐(3‐Indolyl)nitroalkenes: Construction of Trifluoromethylated All‐Carbon Quaternary Stereogenic Centres
Author(s) -
Ma ChunHui,
Kang TaiRan,
He Long,
Liu QuanZhong
Publication year - 2014
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.201402243
Subject(s) - stereocenter , chemistry , enantioselective synthesis , conjugate , indole test , trifluoromethyl , organocatalysis , michael reaction , quaternary carbon , stereochemistry , organic chemistry , catalysis , medicinal chemistry , mathematical analysis , alkyl , mathematics
A family of γ‐nitrobutyric acid esters bearing an all‐carbon quaternary stereogenic centre have been synthesized. Chiral thioureas catalysed the conjugate addition of malonates to nitroalkenes containing a trifluoromethyl and indole motif at the β‐position to afford the corresponding γ‐nitrobutyric acid esters in good yields (up to 89 % yield) and with good to excellent enantioselectivities (up to 90 % ee ). This protocol provides an efficient access to optically enriched γ‐amino acids and β‐disubstituted γ‐butyrolactams.