Premium
Asymmetric anti ‐Selective Michael Reaction of Imidazole‐Modified Ketones with trans ‐β‐Nitroalkenes
Author(s) -
Yang Dongxu,
Wang Linqing,
Li Dan,
Han Fengxia,
Zhao Depeng,
Wang Rui
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405847
Subject(s) - michael reaction , imidazole , chemistry , combinatorial chemistry , organic chemistry , catalysis
The successful application of imidazole‐modified ketones in asymmetric anti ‐selective Michael reactions with trans ‐β‐nitroalkenes is presented by employing a newly developed 3‐bromothiophene‐modified chiral diamine ligand. The corresponding conjugate adduct was submitted to further transformations with Grignard reagents to solve the problem of α‐site selectivity of simple linear ketones. Additionally, the syn ‐selective product was obtained by treating the anti ‐selective adduct with a simple base. In this way, the site‐specific products for both diastereomers in the asymmetric conjugate addition of simple ketones to nitroalkenes can be obtained.