An asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and its applications. Issue 43 (30th October 2017)

• Record Type: Journal Article
• Authors: Hajra, Saumen; Bhosale, Suhas Shivajirao; Hazra, Atanu
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 43(2017)
• Page Start: 9217
• Page End: 9225
• Publication Date: 2017-10-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02407j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A highly efficient TMSOTf-mediated asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and S -phenyl thioacetate was developed to afford the direct synthesis of indole-based β 3, 3 -amino acid thioester with excellent selectivity (dr > 98 : 2). Syntheses of (+)-AG-041R and 3-aminopyrroloindoline have been accomplished utilizing the method. Abstract : A highly efficient TMSOTf-mediated asymmetric acetate-Mannich reaction of isatin derived tert -butylsulfinyl ketimines and S -phenyl thioacetate was developed to afford the direct synthesis of indole-based β 3, 3 -amino acid thioester with excellent selectivity (dr > 98 : 2). Syntheses of (+)-AG-041R and 3-aminopyrroloindoline have been accomplished utilizing the developed method.