Stereoselective Addition of Alkynes to Ketenimines: Copper/Amine Catalyzed Sulfonyl Azide-Alkyne Cycloaddition Reactions for the Synthesis of (Z)-1,3-Enynes

被引：0

作者：

Pothikumar, Rajagopal ^{[1
]}

Sivaraj, Chandrasekaran ^{[1
]}

Giridharan, Kayambu ^{[1
]}

Ravva, Mahesh Kumar ^{[2
]}

Namitharan, Kayambu ^{[1
,3
]}

机构：

[1] SRM Inst Sci & Technol, SRM Res Inst, Dept Chem, Organ Synth & Catalysis Lab, Chennai 603203, Tamil Nadu, India

[2] SRM Univ AP, Dept Chem, Amaravati 522502, Andhra Pradesh, India

[3] Amity Univ, Amity Inst Click Chem Res & Studies, Noida 201301, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 24期

关键词：

CHEMISTRY; COMPONENT; CASCADES; AMIDINES;

D O I：

10.1021/acs.orglett.2c01180

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a copper/amine catalyzed stereoselective addition of alkynes to ketenimine intermediates generated in situ from the sulfonyl azide-alkyne cycloaddition cascade for the stereoselective synthesis of (Z)-1,3-enynes. Significantly, for the first-time, enamine intermediates generated in the copper-catalyzed sulfonyl azide-alkyne cycloaddition reactions have been successfully trapped and isolated as the products. Density functional theory computations have also been performed and found to be consistent with the observed experimental stereoselectivity.

引用

页码：4310 / 4315

页数：6

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