末端炔烃与烯丙基受阻化合物的闭环烯炔复分解反应。

Ring-closing enyne metathesis of terminal alkynes with propargylic hindrance.

作者信息

Laroche Benjamin, Detraz Morgane, Blond Alain, Dubost Lionel, Mailliet Patrick, Nay Bastien

机构信息

†Unité Molécules de Communication et Adaptation des Micro-organismes, Sorbonne Universités, Muséum National d'Histoire Naturelle, Centre National de la Recherche Scientifique (CNRS UMR 7245), 57 rue Cuvier (CP 54), 75005 Paris, France.

‡Unité Structure et instabilité des génomes, Sorbonne Universités, Muséum National d'Histoire Naturelle, Centre National de la Recherche Scientifique (CNRS UMR 7196), Institut National de la Santé et de la Recherche Médicale (INSERM U 1154), 57 rue Cuvier (CP 26), 75005 Paris, France.

出版信息

J Org Chem. 2015 May 15;80(10):5359-63. doi: 10.1021/acs.joc.5b00659. Epub 2015 Apr 28.

DOI:10.1021/acs.joc.5b00659

PMID:25894492

Abstract

The ring closing enyne metathesis of substrates with propargylic hindrance was investigated, revealing the successful combination of the Stewart-Grubbs catalysts and microwave heating sometimes up to 170 °C for oxacycles. Medium-sized rings were obtained from terminal alkynes previously reputed as reluctant substrates. This unmatched combination was applied to the synthesis of carbocycles and oxacycles. In addition, this is the first report on the use of the Stewart Grubbs catalyst in ring closing enyne metatheses.

摘要

对具有炔丙基位阻的底物进行闭环烯炔复分解反应研究，结果表明，斯图尔特-格鲁布斯催化剂与微波加热（有时高达170°C）相结合可成功用于氧杂环的合成。从中等大小的环末端炔烃（以前被认为是难反应的底物）获得了中等大小的环。这种无与伦比的组合被应用于碳环和氧杂环的合成。此外，这是关于斯图尔特-格鲁布斯催化剂在闭环烯炔复分解反应中应用的首次报道。