Heteroatom Nucleophile Induced C-C Fragmentations to Access Functionalized Allenes

被引：1

作者：

Saget, Tanguy ^{[1
]}

Cramer, Nicolai ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, EPFL SB ISIC LCSA, CH-1015 Lausanne, Switzerland

来源：

CHIMIA | 2012年 / 66卷 / 04期

关键词：

Cyclization; Domino reactions; Fragmentation; Radicals; CARBON BOND-CLEAVAGE; ACIDS; CONDENSATION; SEQUENCE;

D O I：

10.2533/chimia.2012.205

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rich structural and reactivity profile of allenes render them versatile synthetic intermediates. However, application of allenes in organic chemistry is often attenuated by inconvenient methods of preparation. Herein we present an operationally simple route to functionalized allenes from vinyl triflate precursors through a Grob-type fragmentation induced by heteroatom nucleophiles such as water, alcohols, thiols or amines. The fragmentation occurs under mild conditions and is well suited for one-pot or domino processes allowing access to a range of synthetically useful intermediates.

引用

页码：205 / 207

页数：3

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