Palladium-Catalyzed Formal (3+2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes

被引：21

作者：

Drew, Melanie A. ^{[1
]}

Tague, Andrew J. ^{[1
]}

Richardson, Christopher ^{[1
]}

Pyne, Stephen G. ^{[1
]}

Hyland, Christopher J. T. ^{[1
]}

机构：

[1] Univ Wollongong, Sch Chem & Mol Biosci, Mol Horizons Res Inst, Wollongong, NSW 2522, Australia

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 12期

关键词：

DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DEAROMATIVE CYCLOADDITION; ORGANOCASCADE SYNTHESIS; DERIVATIVES; 1,3-ENYNES; ACCESS; VINYLCYCLOPROPANES; 3-NITROINDOLES; CONSTRUCTION;

D O I：

10.1021/acs.orglett.1c01364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to give novel cyclic 1,3-dien-5-yne systems from Pd-stabilized zwitterionic 1,3-dipoles and 2-nitro-1,3-enyne substrates. The process is highly atom-efficient and tolerates the reaction of 2-vinyloxirane, 1-tosyl-2-vinylaziridine, and diethyl 2-vinylcyclopropane-1,1-dicarboxylate derived 1,3-dipoles with a variety of 2-nitro-1,3-enyne substrates. The stereochemistry of the intermediate (3 + 2) cycloadducts was determined by single crystal X-ray analysis. Furthermore, a selective kinetic elimination of the cycloadduct with an antiperiplanar relationship between the NO2 group and the participating hydrogen was demonstrated, allowing for efficient isolation of a single diastereoisomer of the cycloadduct.

引用

页码：4635 / 4639

页数：5

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