通过钌催化的烯-炔-烯复分解反应，从3,4-双烯丙氧基-丁-1-炔衍生物中选择性合成手性二氧杂双环[4.4.0]癸烷和二氧杂双环[5.3.0]癸烷。
Selective synthesis of chiral dioxabicyclo[4.4.0]decane and dioxabicyclo[5.3.0]decane from 3,4-bisallyloxy-but-1-yne derivatives via ruthenium-catalyzed en-yn-ene metathesis.
作者信息
Wu Chang-Jung, Madhushaw Reniguntala J, Liu Rai-Shung
机构信息
Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, 30043, ROC.
出版信息
J Org Chem. 2003 Oct 3;68(20):7889-92. doi: 10.1021/jo0301548.
We prepared a series of chiral 3,4-bisallyloxy-but-1-ynes having syn and anti configurations. Treatment of these substrates with Grubbs catalyst Cl2(PCy3)2Ru=CHPh (3 mol %) preferably gave chiral dioxabicyclo[4.4.0]decane (yields > 55%) in addition to dioxabicyclo[5.3.0]decane in minor proportions. On substitution of the 4-allyloxy group of these substrates with a 4-but-2-enyloxy group, the metathesis reactions produced only dioxabicyclo[5.3.0]decane in the presence of Grubbs ruthenium-imidazolidene carbene catalyst.
我们制备了一系列具有顺式和反式构型的手性3,4-双烯丙氧基-丁-1-炔。用格拉布催化剂Cl2(PCy3)2Ru=CHPh（3摩尔%）处理这些底物时，除了少量的二氧杂双环[5.3.0]癸烷外，主要生成了手性二氧杂双环[4.4.0]癸烷（产率>55%）。将这些底物的4-烯丙氧基用4-丁-2-烯氧基取代后，在格拉布钌-咪唑啉卡宾催化剂存在下进行复分解反应，只生成了二氧杂双环[5.3.0]癸烷。
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