Sc(OTf)₃/TsOH: a highly efficient catalytic system for the synthesis of 2,6-dioxabicyclo[3,2,1]octane derivatives

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• 作者：B.V. Subba Reddy^a ; ^{basireddy@iict.res.in} ; G. Narasimhulu^a ; Y. Vikram Reddy^a ; P.P. Chakravarthy^a ; J.S. Yadav^a ; B. Sridhar^b
• 关键词：Intramolecular Prins cyclization ; Co-operative catalysis ; Cascade reactions ; 2 ; 6-Dioxabicyclo[3 ; 2 ; 1]octane scaffolds
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：13 June, 2012
• 卷：53
• 期：24
• 页码：3100-3103
• 文件大小：3153 K

摘要

A variety of aldehydes undergo a tandem acetalization and intramolecular Prins cyclization with pent-4-ene-1,2-diol in the presence of 5 mol %scandium triflate and 15 mol %p-toluenesulfonic acid (TsOH) in dichloroethane at 80 掳C to produce the corresponding bicyclic ethers, that is, 2,6-dioxabicyclo[3,2,1]octane derivatives in good yields and with high selectivity. The salient features of this methodology are higher yields, lower catalyst loadings, and faster reaction times. The combination of Sc(OTf)₃ and TsOH (1:3) was found to be more effective than either Sc(OTf)₃ or TsOH alone.