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

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

Authors :
Subba Reddy, B.V.
Narasimhulu, G.
Vikram Reddy, Y.
Chakravarthy, P.P.
Yadav, J.S.
Sridhar, B.
Source :
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jun2012, Vol. 53 Issue 24, p3100-3103. 4p.
Publication Year :
2012

Abstract

Abstract: A variety of aldehydes undergo a tandem acetalization and intramolecular Prins cyclization with pent-4-ene-1,2-diol in the presence of 5mol% scandium triflate and 15mol% p-toluenesulfonic acid (TsOH) in dichloroethane at 80°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. [Copyright &y& Elsevier]

Details

Language :
English
ISSN :
00404039
Volume :
53
Issue :
24
Database :
Academic Search Index
Journal :
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :
Academic Journal
Accession number :
75168403
Full Text :
https://doi.org/10.1016/j.tetlet.2012.04.029