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
收藏
页码：3700 / 3706
页数：7
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