The utility of vinyl ethers and vinyl esters in the Khand reaction. The value of vinyl esters as ethylene equivalents and a modified synthesis of (+)-taylorione as an example
The utility of vinyl ethers and vinyl esters in the Khand reaction. The value of vinyl esters as ethylene equivalents and a modified synthesis of (+)-taylorione as an example
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DOI：
10.1016/s0022-328x(01)00891-9
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发表时间：
2001-07-02
影响因子：
2.3
通讯作者：
Robertson, SM
中科院分区：
文献类型：
--
作者：
Kerr, WJ;McLaughlin, M;Robertson, SM
研究了各种含氧烯烃在Khand环化反应中的行为。尽管几种乙烯基醚反应得到预期的氧化环戊烯酮产物，通常具有良好的区域选择性水平，但发现乙烯基酯的使用提供了作为主要产物的还原环戊烯酮，其中碳-氧键已断裂。这种意想不到的反应被开发成在Khand反应中使用乙烯气体的替代方法，并且发现其适用于各种炔底物。然后将该方法扩展为天然产物（+）-taylorione（和（+）-nortaylorione）合成中的关键步骤。(C)2001年爱思唯尔科学B。V.保留所有权利。
The behaviour of various oxygenated alkenes in the Khand cyclisation reaction has been studied. Although several vinyl ethers reacted to give the expected oxygenated cyclopentenone products, usually with good levels of regioselectivity, the use of vinyl esters was found to afford, as the major products, reduced cyclopentenones in which the carbon-oxygen bond had been cleaved. This unexpected reaction was developed into an alternative procedure to using ethylene gas in the Khand reaction and was found to be applicable with a variety of alkyne substrates. The method was then extended to form the key step in the synthesis of the natural product (+)-taylorione (and (+)-nortaylorione). (C) 2001 Elsevier Science B. V. All rights reserved.