Bifunctional Iminophosphorane Catalyzed Amide Enolization for Enantioselective Cyclohexadienone Desymmetrization

被引：4

作者：

Poh, Charmaine Y. X. ^{[1
]}

Rozsar, Daniel ^{[1
]}

Yang, Jinchao ^{[1
]}

Christensen, Kirsten E. ^{[1
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2024年 / 63卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric catalysis; C-C bond formation; conjugate Addition; enantioselectivity; organocatalysis; SULFA-MICHAEL ADDITION; ASYMMETRIC TRANSFORMATIONS; CRYSTAL-STRUCTURES; ALKYL THIOLS; ALPHA; ACIDITIES; ESTERS;

D O I：

10.1002/anie.202315401

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The organocatalytic enolization of 2-arylacetamides, followed by an enantioselective intramolecular conjugate addition to tethered 2,5-cyclohexadienones, yielding 3D fused N-heterocycles, is described. The transformation represents the first strong activating group-free activation of carboxamides via alpha-C-H deprotonation in a metal-free, catalytic, and enantioselective reaction, and is achieved by employing a bifunctional iminophosphorane (BIMP) superbase. The enolization of 2-arylacetamides, followed by an enantioselective intramolecular conjugate addition to tethered 2,5-cyclohexadienones, yielding saturated fused N-heterocycles, is described. The transformation is achieved by employing a bifunctional iminophosphorane (BIMP) superbase catalyst and represents the first unactivated carboxamide deprotonation in a metal-free, catalytic, and enantioselective transformation.image

引用

页数：6

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