Mild and efficient tetrahydropyranylation of alcohols-catalysis by lithium perchlorate in diethyl ether
Treatment of 3,4-dihydropyran 1 with various alcohols 2 – 9 furnished the tetrahydropyranyl ethers 10–17 in the
References (12)
- et al.
Tetrahedron Lett.
(1988) - et al.
J. Org. Chem.
(1996) - et al.
Protective Groups in Organic Synthesis
Encyclopedia of Reagents for Organic synthesis
(1995)- et al.
Synthesis
(1985) - et al.
Synthesis
(1986)
Cited by (66)
Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations
2016, European Journal of Organic ChemistryAddition of H_X Reagents to Alkenes, Alkynes, and Allenes without Transition Metal
2014, Comprehensive Organic Synthesis: Second EditionAllyl tetrahydropyranyl ether: a versatile alcohol/thiol protecting reagent
2009, Tetrahedron LettersN,N′-Dibromo-N,N′-1,2-ethanediylbis(benzene sulfonamide) as a novel N-bromo reagent catalyzed tetrahydropyranylation/depyranylation of alcohols and phenols under mild conditions
2007, Catalysis CommunicationsCitation Excerpt :There are several known methods for the tetrahydropyranylation and depyranylation of alcohols [3]. The most commonly used reagents that can catalyze the protection and deportection of both transformations are p-toluenesulfonic acid (PTSA) [4,5], pyridinium p-toluenesulfonate (PPTS) [6], NH4Cl [7], acetonyltriphenylphosphonium bromide [8], I2[9,10], LiBr [11], ZrCl4[12], tetrabutylammonium tribromide [13], Fe(ClO4)3[14], K5CoW12O40 · 3H2O [15], PdCl2(CH3CN)2[16], trichloroisocyanuric acid [17], silica sulfuric acid [18], Bi(NO3)3 · 5H2O [19], aqueous zinc tetrafluoroborate [20], and AlCl3 · 6H2O [21]. However, in most cases these procedures suffer from one or more disadvantages such as stringent conditions, elevated reaction temperatures, longer reaction times, and expensive reagents.