Iodine-catalyzed prins cyclization of homoallylic alcohols and aldehydes.

ABSTRACT: The iodine-catalyzed Prins cyclization of homoallylic alcohols and aldehydes was investigated under metal-free conditions and without additives. Anhydrous conditions and inert atmosphere are not required. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol and 21 aldehydes (aliphatic and aromatic) in CH₂Cl₂ in the presence of 5 mol % of iodine gave 1,4,5,6-tetrahydro-2H-benzo[f]isochromenes in 54%-86% yield. Under similar conditions, the Prins cyclization of six alcohols containing an endocyclic double bond (primary, secondary, or tertiary) led to dihydropyrans in 52%-91% yield. The acyclic homoallylic alcohols gave 4-iodo-tetrahydropyran in 29%-41% yield in the presence of 50 mol % of iodine. This type of substrate is the main limitation of the methodology. The relative configuratio

SUBMITTER: Reddy KR 

PROVIDER: S-EPMC6269844 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature