title: Highly diastereoselective Friedel-Crafts reaction of arenes with N-tert-butanesulfinylimino ester towards the efficient synthesis of α-arylglycines.
abstract: Lewis acid-catalyzed highly diastereoselective asymmetric Friedel-Crafts alkylation of arenes with a chiral N-tert-butanesulfinylimino ester is described. The reaction can be accomplished with ease in the presence of a catalytic amount of In(OTf)(3) at room temperature, providing a series of enantiomerically enriched α-arylglycines in good yields and with excellent diastereoselectivities (up to 99% de). Highly stereoselective double Friedel-Crafts alkylation to afford dialkylation product was also investigated.
authors: State key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, People's Republic of China.
authors: Yi
authors: Y
authors: Li
authors: Du-Ming
authors: DM
authors: Ji
authors: Ming-Hua
authors: MH
authors: Xu
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; C481933:N-tert-butanesulfinylimino ester; D013452:Sulfonium Compounds; D005998:Glycine