Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.
Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.
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DOI：
10.1021/jo201478d
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发表时间：
2011-11-18
影响因子：
3.6
通讯作者：
Pike, Robert D.
中科院分区：
文献类型：
--
作者：
Lambert, R. Frederick;Hinkle, Robert J.;Ammann, Stephen E.;Lian, Yajing;Liu, Jia;Lewis, Shane E.;Pike, Robert D.
催化量的三氟甲磺酸铋（III）有效地引发环氧化物重排成醛，醛随后与（Z）-δ-羟基烯基硅烷反应得到2，6-二取代-3，6-二氢-2H-吡喃。将使用Bi（OTf）3的所需产物的分离产率与在存在和不存在几种添加剂的情况下用TfOH和TMSOTf进行反应时的产率进行比较。这些研究，以及NMR光谱分析，表明初始刘易斯酸/碱之间的相互作用Bi（OTf）3和基板提供TfOH原位。
Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes which subsequently react with (Z)-δ-hydroxyalkenylsilanes to afford 2,6-disubstituted-3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)3 were compared with yields when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)3 and substrates providing TfOH in situ.
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影响因子：
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