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

被引：49

作者：

Suc, Josipa ^{[1
]}

Dokli, Irena ^{[1
]}

Gredicak, Matija ^{[1
]}

机构：

[1] Rudjer Boskovic Inst, Div Organ Chem & Biochem, Bijenicka C 54, Zagreb 10000, Croatia

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 10期

关键词：

CONJUGATE ADDITION; N-ACYL; THIOLS; DESYMMETRIZATION;

D O I：

10.1039/c5cc08813e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 Bronsted 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.

引用

页码：2071 / 2074

页数：4

共 43 条

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