One-pot enyne ring-closing metathesis-Diels-Alder reactions for the synthesis of polycyclic sulfamides

被引：7

作者：

Hill-Cousins, Joseph T. ^{[1
]}

Salim, Sofia S. ^{[1
]}

Bakar, Youssef M. ^{[1
]}

Bellingham, Richard K. ^{[2
]}

Light, Mark E. ^{[1
]}

Brown, Richard C. D. ^{[1
]}

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

[2] GlaxoSmithKline, Dept Synthet Chem, Chem Dev, Tonbridge TN11 9AN, Kent, England

来源：

TETRAHEDRON | 2014年 / 70卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

Metathesis; Enyne; Sulfamide; Diels-Alder; One-pot; SOLID-PHASE SYNTHESIS; NATURAL-PRODUCTS; ACID; ISOMERIZATION; DERIVATIVES; STRATEGIES;

D O I：

10.1016/j.tet.2014.04.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-closing metathesis (RCM) and sequential Yb(OTf)(3) promoted Diels-Alder reactions of sulfamide-linked enynes proceeded selectively in one-pot-to afford-a series of bicyclic and tricyclic sulfamides. Excellent levels of diastereoselectivity are observed for the cycloaddition step, with only the endo-adducts being isolated. The protocol was further extended to incorporate a one-pot RCM-cross metathesis (CM)-Diels-Alder sequence, permitting rapid access to high levels of molecular complexity from simple and easily accessible precursors. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

引用

页码：3700 / 3706

页数：7

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