32360-30-8Relevant academic research and scientific papers
Cu-Catalyzed Intramolecular Amidation of Unactivated C(sp3)-H Bonds to Synthesize N-Substituted Indolines
Pan, Fei,Wu, Bin,Shi, Zhang-Jie
supporting information, p. 6487 - 6490 (2016/05/02)
A copper-catalyzed intramolecular amidation of unactivated C(sp3)-H bonds to construct indoline derivatives has been developed. Such an amidation proceeded well at primary C-H bonds preferred to secondary C-H bonds. The transformation owned a b
A chiral axis due to an acyclic imide-Ar bond: A study of steric effects of acyl groups on racemization
Kondo, Kazuhiro,Iida, Takeko,Fujita, Hiroko,Suzuki, Tomoko,Yamaguchi, Kentaro,Murakami, Yasuoki
, p. 8883 - 8891 (2007/10/03)
Studies on the racemization in a series of optically active compounds 3a-e, including the steric effect of their acyl groups, are described. The first example of optically active compounds 3c and 3d, which possess axial chirality based on an acyclic imide-Ar bond, has been reported. A quite interesting result has been revealed, namely, that 3a bearing a bulky acyl group rather than a relatively small one racemized more easily. To explain this observed phenomenon, 13C NMR experiments and the reaction with benzylamine of 3a-e were undertaken. These results suggested that the t-BuCO-N bond in 3a which racemized easily, is more twisted, compared with the RCO-N bonds in 3b-e which are relatively stable to racemization. Furthermore, the absolute configuration of 3b and 3c has been determined to be R by the CD spectrum and the X-ray crystallographic analysis of racemic 3f has been accomplished. (C) 2000 Published by Elsevier Science Ltd.
Atropisomeric amides: Stereoselective enolate chemistry and enantioselective synthesis via a new SmI2-mediated reduction
Hughes, Adam D.,Price, David A.,Simpkins, Nigel S.
, p. 1295 - 1304 (2007/10/03)
The use of certain types of atropisomeric amides, incorporating an N-MEM-ortho-tert-bityariume group, for stereoselective reactions, has been explored. Enolate reactions of these systems are highly diastereocontrolled, and enantiomerically enriched starting materials can be obtained, starting from lactic acid, via a new SmI2 mediated reduction process.
SmI2-mediated reduction of α-functionalised amides: Highly enantiospecific access to an atropisomeric amide
Hughes, Adam D.,Simpkins, Nigel S.
, p. 967 - 968 (2007/10/03)
SmI2 or SmI2-LiCl mixtures can be used to reduce α-functionalised amides in yields of up to 85% depending upon the amide structure. The method has been applied to the synthesis of an atropisomeric anilide system in highly enantioenriched form, starting with (S)-O-acetyl lactic acid.
