N-Heterocyclic carbene catalyzed base assisted C-C bond cleavage of cyclopropenones: an approach towards diastereoselective synthesis of azetidinones and benzoxazepines

被引：4

作者：

Nanda, Tanmayee ^{[1
,2
]}

Shukla, Asish Dharmendra ^{[1
,2
]}

Dhal, Shubham Kumar ^{[1
,2
]}

Fastheem, Muhammed ^{[1
,2
]}

Ravikumar, Ponneri C. ^{[1
,2
]}

机构：

[1] Natl Inst Sci Educ & Res NISER, Sch Chem Sci, Bhubaneswar 752050, Odisha, India

[2] Homi Bhabha Natl Inst, Training Sch Complex, Mumbai 400094, India

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 24期

关键词：

3+2 CYCLOADDITION; ACTIVATION; CASCADE; ESTERS; ACCESS;

D O I：

10.1039/d3qo01328f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Heterocyclic carbene catalyzed base assisted diastereoselective ring opening of diphenyl-cyclopropenone followed by ring-closing through [3 + 1] or [3 + 4] addition with o-aminophenol furnished biologically important scaffolds azetidinones or benzoxazepines, respectively. The unique feature of this reaction is that the key intermediate acylazolium species is generated through C-C bond cleavage of cyclopropenone rather than routine substrates such as conjugated enals, ynals and acyl halides. Interestingly, this reaction involves an alpha-aryl substituted acylazolium species, which has never been reported so far with respect to N-heterocyclic carbene catalysis. We have demonstrated a synthetic protocol to synthesize two different bio-active skeletons, that is, beta-lactam and benzoxazepine by using N-heterocyclic carbene as the catalyst. Herein, 3-membered strained cyclopropenone has been used as a 3C synthon.

引用

页码：6166 / 6171

页数：6

共 22 条

[1] Nickel(0)-Catalyzed Enantioselective [3+2] Annulation of Cyclopropenones and α,β-Unsaturated Ketones/Imines [J].