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An expeditious synthesis of hexahydrobenzo[f]isochromenes and of hexahydrobenzo[f]isoquinoline via iodine-catalyzed Prins and aza-Prins cyclization

✍ Scribed by Luiz F. Silva Jr.; Samir A. Quintiliano

Book ID: 104096376
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 997 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.02.202

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✦ Synopsis

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.

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