Synthesis of enantiomerically pure 2,3,4,6-tetrasubstituted tetrahydropyrans by prins-type cyclization of methyl ricinoleate and aldehydes

被引：46

作者：

Biermann, Ursula ^{[1
]}

Luetzen, Arne ^{[1
]}

Metzger, J. rgen O. ^{[1
]}

机构：

[1] Univ Oldenburg, Inst Pure & Appl Chem, D-26111 Oldenburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 11期

关键词：

aldehydes; chiral pool; cyclization; diastereoselectivity; renewable feedstocks; tetrahydropyrans;

D O I：

10.1002/ejoc.200500701

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The AlCl3-catalyzed Prins-type cyclization of methyl ricinoleate (1), an enantiomerically pure renewable compound, with aldehydes such as heptanal (2a), isobutyraldehyde (2b), pivaldehyde (2c) and benzaldehyde (2d) is a simple reaction for the diastereoselective synthesis of enantiomerically pure 2,3,6-trialkyl-substituted 4-chlorotetrahydropyrans. The respective 4-hydroxytetrahydropyrans are obtained e.g. with aldehydes 2a and 2d using montmorillonite KSF/O as the catalyst. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

引用

页码：2631 / 2637

页数：7

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