Relay Catalysis-Enabled Enantioselective Annulations of β,γ-Alkynyl-α-imino Esters with 1,3-Diones for the Divergent Synthesis of Chiral Oxacycles

被引：0

作者：

Khajuria, Chhavi ^{[1
]}

Saini, Nidhi ^{[1
]}

Gupta, Khushboo ^{[1
]}

Singh, Vinod K. ^{[1
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 08期

关键词：

INHIBITORS;

D O I：

10.1021/acs.orglett.5c00233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel protocol for the chemically divergent synthesis of chiral oxacycles has been developed using organo/metal relay catalysis. The methodology integrates a stereospecific Mannich reaction between beta,gamma-alkynyl-alpha-imino esters and 1,3-diones catalyzed by a chiral bifunctional squaramide, followed by Lewis acid-catalyzed regioselective annulation reactions. By switching the Lewis acid employed, we achieved a divergent pathway to construct structurally related pyran and furan derivatives from a common intermediate. The (3+3) and (3+2) annulation products were obtained in high yields and excellent stereoselectivities. Comprehensive mechanistic studies were conducted to establish the reaction mechanism.

引用

页码：1955 / 1960

页数：6