116407-57-9Relevant academic research and scientific papers
Asymmetric Synthesis of Functionalized Cyclopropanes via β-Lithiation-Cyclization of N-Monosubstituted 3-(Phenylthio)-2-propanamides
Tanaka, Kazuhiko,Funaki, Ikuo,Kaji, Aritsune,Minami, Keizaburo,Sawada, Masami,Tanaka, Takanori
, p. 7185 - 7188 (2007/10/02)
The reaction of N--3-(phenylthio)-2-propanamide with 4 equiv of n-BuLi gives exclusively trans cyclopropanes in 94 percent yield (ratio of diastereomers 1:3).The use of the triisopropylsilyl ether of the amide led to high diastereoselectivity (ratio 1:11) in this cyclopropanation.The absolute configuration of the resulting diastereomeric cyclopropane was determined by X-ray crystallography.The β-lithiation and subsequent alkylation of the cyclopropanes provided a wide variety of optically pure cyclopropane derivatives.
