Base mediated aza-[2+1] annulation and regioselective aziridine ring-opening cascade: mild synthesis of functionalized β-amino ketones from cyclic N-sulfonyl aldimines and α-carbonyl sulfonium salts

被引：0

作者：

Lei, Xiaoqiang ^{[1
]}

Sun, Yanyan ^{[1
]}

Guo, Qinglan ^{[1
]}

Shi, Jiangong ^{[1
]}

机构：

[1] Chinese Acad Med Sci & Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Inst Mat Med, Beijing 100050, Peoples R China

来源：

RSC ADVANCES | 2024年 / 14卷 / 24期

基金：

中国国家自然科学基金; 美国国家科学基金会;

关键词：

DECARBOXYLATIVE MANNICH REACTION; RHODIUM-CATALYZED ADDITION; AZA-MICHAEL ADDITION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SUPERIOR ELECTROPHILES; 1,3-AMINO ALCOHOLS; BROAD SCOPE; ACCESS; IMINES;

D O I：

10.1039/d4ra02817a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclic N-sulfonyl aldimines are well-known aza-[2C]-synthons for various [2 + n] annulation reactions. Herein we describe a novel base mediated [2 + 1] annulation and a regioselective aziridine ring-opening reaction cascade, which provides an efficient and distinct synthetic strategy from readily available cyclic N-sulfonyl aldimines and alpha-carbonyl sulfonium salts leading to beta-amino ketone derivatives through the corresponding fused tri-substituted aziridines. This one-pot, two-step process involves formation of C-C and C-N bonds and subsequent cleavage of a C-N bond. The features of the developed reaction include the use of mild reaction conditions, broad substrate scope, and excellent yields. The synthetic utility of this approach was demonstrated by gram-scale operation and further product derivatizations.

引用

页码：17178 / 17183

页数：6