Issue 9, 2017

Diastereoselective synthesis of tetrahydropyrans via Prins–Ritter and Prins–arylthiolation cyclization reactions

Abstract

An efficient method has been developed for the synthesis of two new classes of tetrahydropyran derivatives comprising amide, tetrazole or benzothiazole moieties via a three-component reaction of 6-methylhept-5-en-2-ol, arylaldehydes and nitriles/thiols in the presence of a tetrafluoroboric acid diethyl ether complex. The reaction proceeds via the formation of an oxocarbenium ion. This protocol is highly diastereoselective and only single diastereomer has been isolated in each case.

Graphical abstract: Diastereoselective synthesis of tetrahydropyrans via Prins–Ritter and Prins–arylthiolation cyclization reactions

Supplementary files

Article information

Article type
Paper
Submitted
09 Dec 2016
Accepted
01 Feb 2017
First published
01 Feb 2017

Org. Biomol. Chem., 2017,15, 2003-2012

Diastereoselective synthesis of tetrahydropyrans via Prins–Ritter and Prins–arylthiolation cyclization reactions

N. Hazarika, B. Sarmah, M. Bordoloi, P. Phukan and G. Baishya, Org. Biomol. Chem., 2017, 15, 2003 DOI: 10.1039/C6OB02692C

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