A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

被引：6

作者：

Joyce, Liam M. ^{[1
]}

Drew, Melanie A. ^{[1
]}

Tague, Andrew J. ^{[1
]}

Thaima, Thanaphat ^{[1
]}

Gouranourimi, Ali ^{[2
]}

Ariafard, Alireza ^{[2
]}

Pyne, Stephen G. ^{[1
]}

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

机构：

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

[2] Univ Tasmania, Sch Phys Sci, Hobart, Tas 7018, Australia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 12期

基金：

澳大利亚研究理事会;

关键词：

1; 6-allenyne; Alder-ene; cycloisomerization; lactam; computations; INTRAMOLECULAR 2+2 CYCLOADDITION; GOLD-CATALYZED CYCLOISOMERIZATION; ALLENE; CYCLIZATION; ACTIVATION; CONSTRUCTION; SUBSTITUENT; LACTONES; NITROGEN;

D O I：

10.1002/chem.202104022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermally induced cycloisomerization reactions of 1,6-allenynes gives alpha-methylene-gamma-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.

引用

页数：5

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