Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl), S-acetals. Issue 10 (21st December 2015)

• Record Type: Journal Article
• Authors: Suć, Josipa; Dokli, Irena; Gredičak, Matija
• Is Part Of: Chemical communications. Volume 52:Issue 10(2016)
• Page Start: 2071
• Page End: 2074
• Publication Date: 2015-12-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc08813e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Chiral Brønsted acid catalyzed synthesis of N (acyl), S -acetals from in situ generated ketimines proceeds in high yields and enantioselectivities. Abstract : The first organocatalytic asymmetric addition of thiols to N -acyl ketimines, which are generated in situ from 3-hydroxy isoindolinones, is described. The reaction proceeds smoothly with a broad range of ketimines and thiols using a chiral Brønsted acid catalyst to afford N (acyl), S -acetals comprising a tetrasubstituted stereocenter in high yields and enantioselectivities (up to 98.5 : 1.5 e.r.). The usefulness of the developed protocol is demonstrated in the synthesis of a known HIV-1 reverse transcriptase inhibitor.