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Molecules 2013, 18(9), 11100-11130; doi:10.3390/molecules180911100

Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes

Jr. 1,*
1 Instituto de Química - Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil 2 Laboratório de Cristalografia, Instituto de Química, Universidade Federal de Alfenas, Rua Gabriel Monteiro da Silva 714, 37130-000 Alfenas, Minas Gerais, Brazil
* Author to whom correspondence should be addressed.
Received: 24 July 2013 / Revised: 6 August 2013 / Accepted: 23 August 2013 / Published: 10 September 2013
(This article belongs to the Section Organic Synthesis)
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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 configuration of the products was assigned by NMR and X-ray analysis. The mechanism and the ratio of the products are discussed, based on DFT calculations.
Keywords: isochromene; pyrans; prins cyclization; iodine; DFT calculations isochromene; pyrans; prins cyclization; iodine; DFT calculations
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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Reddy, K.R.K.K.; Rosa, I.M.L.; Doriguetto, A.C.; Bastos, E.L.; Silva, L.F., Jr. Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes. Molecules 2013, 18, 11100-11130.

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