An expeditious synthesis of hexahydrobenzo[f]isochromenes and of hexahydrobenzo[f]isoquinoline via iodine-catalyzed Prins and aza-Prins cyclization
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
20/10/2012
20/10/2012
2009
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| Resumo |
Homoallylic alcohols (primary, secondary, or tertiary containing an endocyclic or an exocyclic double bond) react with equimolar amounts of aldehydes (aliphatic or aromatic) and ketones (aliphatic) in the presence of 5 mol % of iodine. This Prins cyclization was used in the preparation of hexahydrobenzo[f]isochromenes and of a 4-hydroxy-tetrahydropyran, in 54-81% yield. The procedure is also efficient for an aza-Prins cyclization of a homoallylic sulfonamide and benzaldehyde, producing a hexahydrobenzo[f]isoquinoline. (C) 2009 Elsevier Ltd. All rights reserved. Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) FAPESP Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) CNPq |
| Identificador |
TETRAHEDRON LETTERS, v.50, n.19, p.2256-2260, 2009 0040-4039 http://producao.usp.br/handle/BDPI/31519 10.1016/j.tetlet.2009.02.202 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Tetrahedron Letters |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #SPONGE PHORBAS SP #HOMOALLYLIC ALCOHOLS #MOLECULAR-IODINE #RING CONTRACTION #STEREOSELECTIVE-SYNTHESIS #TETRAHYDROPYRAN RINGS #LEUCASCANDROLIDE-A #VERSATILE REAGENT #LEAD(IV) ACETATE #FRAGMENTATION #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
