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

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• 作者：Joseph T. Hill-Cousins^a ; Sofia S. Salim^a ; Youssef M. Bakar^a ; Richard K. Bellingham^b ; Mark E. Light^a ; Richard C.D. Brown^a ; ^{rcb1@soton.ac.uk" class="auth_mail} ; ^{R.C.Brown@soton.ac.uk" class="auth_mail}
• 关键词：Metathesis ; Enyne ; Sulfamide ; Diels&ndash ; Alder ; One-pot
• 刊名：Tetrahedron
• 出版年：10 June 2014
• 年：2014
• 卷：70
• 期：23
• 页码：3700-3706
• 全文大小：1227 K

文摘

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.