Issue 10, 2016

Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals

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.

Graphical abstract: Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals

Supplementary files

Article information

Article type
Communication
Submitted
23 Oct 2015
Accepted
04 Dec 2015
First published
07 Dec 2015

Chem. Commun., 2016,52, 2071-2074

Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals

J. Suć, I. Dokli and M. Gredičak, Chem. Commun., 2016, 52, 2071 DOI: 10.1039/C5CC08813E

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