Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes

被引：9

作者：

Reddy, Kachi R. Kishore Kumar ^{[1
]}

Rosa, Iara M. L. ^{[2
]}

Doriguetto, Antonio C. ^{[2
]}

Bastos, Erick L. ^{[1
]}

Silva, Luiz F., Jr. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05513970 Sao Paulo, Brazil

[2] Univ Fed Alfenas, Inst Quim, Lab Cristalog, BR-37130000 Alfenas, MG, Brazil

来源：

MOLECULES | 2013年 / 18卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

isochromene; pyrans; prins cyclization; iodine; DFT calculations; ENVIRONMENTALLY BENIGN SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; EXPEDITIOUS SYNTHESIS; TETRAHYDROPYRAN; THALLIUM(III); KETONES; INDANS; LEWIS; ACIDS;

D O I：

10.3390/molecules180911100

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：11100 / 11130

页数：31

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