Synthesis of Tetrahydrofurans by Cyclization of Homoallylic Alcohols with Iodine/Iodine(III)
Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
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Data(s) |
20/10/2012
20/10/2012
2011
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Resumo |
Tetrahydrofuran derivatives can be obtained by cyclo-functionalization of homoallylic alcohols bearing a terminal double bound by using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser`s reagent) in the presence of a catalytic amount of 12 (20 mol %) in MeOH under mild conditions. This transformation is an overall 5-endo-trig cyclization, which occurs by two different pathways. The first is a 4-exo-trig cyclization followed by ring expansion, whereas the second is an electrophilic addition followed by a 5-endo-tet cyclization. FAPESP Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) CNPq Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) CAPES |
Identificador |
JOURNAL OF ORGANIC CHEMISTRY, v.76, n.5, p.1499-1502, 2011 0022-3263 http://producao.usp.br/handle/BDPI/31386 10.1021/jo102413u |
Idioma(s) |
eng |
Publicador |
AMER CHEMICAL SOC |
Relação |
Journal of Organic Chemistry |
Direitos |
restrictedAccess Copyright AMER CHEMICAL SOC |
Palavras-Chave | #HYPERVALENT IODINE REAGENTS #STEREOSELECTIVE-SYNTHESIS #CYCLIC ETHERS #IODOTOLUENE DIFLUORIDE #UNSATURATED ALCOHOLS #CARBOXYLIC-ACIDS #ALKENOIC ACIDS #RING-EXPANSION #DERIVATIVES #<HYDROXY(TOSYLOXY)IODO>BENZENE #Chemistry, Organic |
Tipo |
article original article publishedVersion |