Stereoelectronic Effects on Dienophile Separation Influence the Diels-Alder Synthesis of Molecular Clefts

被引：0

作者：

Stoermer, Martin J. ^{[1
]}

Wickramasinghe, Wasantha A. ^{[1
]}

Byriel, Karl A. ^{[1
]}

Hockless, David C. R. ^{[2
]}

Skelton, Brian W. ^{[2
]}

Sobolev, Alexandre N. ^{[2
]}

White, Allan H. ^{[2
]}

Mak, Jeffrey Y. W. ^{[1
]}

Fairlie, David P. ^{[1
]}

机构：

[1] Univ Queensland, Inst Mol Biosci, Div Chem & Struct Biol, St Lucia, Qld 4072, Australia

[2] Univ Western Australia, Sch Mol Sci, Perth, WA 6009, Australia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 45期

基金：

澳大利亚研究理事会;

关键词：

Diene; Cavity; Host-guest systems; Solid-state structures; Pi interactions; HYDROGEN-BONDS; CH/PI INTERACTION; PI INTERACTION; RECOGNITION; TWEEZERS; STEREOSELECTIVITY; COMPLEXATION; H-1-NMR; DESIGN; WATER;

D O I：

10.1002/ejoc.201701319

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formal cycloaddition adduct of 1,4-benzoquinone with two equivalents of cyclopentadiene is a scaffold with two non-conjugated alkenes. Both alkenes undergo endo [4+2] cycloaddition with a diene to form a rigid U-shaped molecular cleft. Here we show experimental, computational and structural evidence that interactions between the alkenes affect structural rigidity, Diels-Alder reactivity, cleft formation and host-guest capture.

引用

页码：6793 / 6796

页数：4

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