246872-11-7Relevant academic research and scientific papers
Mapping the active site in a chemzyme: Diversity in the N-substituent in the catalytic asymmetric aziridination of imines
Zhang, Yu,Lu, Zhenjie,Desai, Aman,Wulff, William D.
supporting information; experimental part, p. 5429 - 5432 (2009/06/20)
(Chemical Equation Presented) The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)3 is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.
Preparation of primary amines by the alkylation of O-sulfonyloximes of benzophenone derivatives with Grignard reagents
Tsutsui, Hironori,Ichikawa, Tomoko,Narasaka, Koichi
, p. 1869 - 1878 (2007/10/03)
Primary amines are prepared by the electrophilic amination of Grignard reagents with benzophenone O-sulfonyloxime derivatives. 4,4'- Bis(trifluoromethyl)benzophenone O-sulfonyloximes react with alkyl Grignard reagents in the presence of a catalytic amount of CuCN in tetrahydrofuran- hexamethylphosphoric triamide to give N-alkylimines, which are readily hydrolyzed to primary amines. 3,3',5,5'-Tetrakis(trifluoromethyl)benzophenone O-p-tolylsulfonyloxime is arylated to the corresponding N-arylimines with aryl Grignard reagents in ether-toluene, and hydrolysis of the resulting imines gives aniline derivatives.
