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

Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes

1email, 2email, 2email, 1email and Jr. 1,* email
Received: 24 July 2013; in revised form: 6 August 2013 / Accepted: 23 August 2013 / Published: 10 September 2013
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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 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
PDF Full-text Download PDF Full-Text [1554 KB, uploaded 18 June 2014 20:11 CEST]

Export to BibTeX |

MDPI and ACS Style

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.

AMA Style

Reddy KRKK, Rosa IML, Doriguetto AC, Bastos EL, Silva LF, Jr. Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes. Molecules. 2013; 18(9):11100-11130.

Chicago/Turabian Style

Reddy, Kachi R.K.K.; Rosa, Iara M.L.; Doriguetto, Antônio C.; Bastos, Erick L.; Silva, Luiz F., Jr. 2013. "Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes." Molecules 18, no. 9: 11100-11130.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert