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Stereoselective synthesis of 2,4,5-trisubstituted tetrahydropyrans using an intramolecular allylation strategy

Jervis, Peter J., Kariuki, Benson and Cox, Liam R. 2006. Stereoselective synthesis of 2,4,5-trisubstituted tetrahydropyrans using an intramolecular allylation strategy. Organic Letters 8 (20) , pp. 4649-4652. 10.1021/ol061957v

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Abstract

A highly stereoselective route to 2,4,5-trisubstituted tetrahydropyrans is reported. The key step employs an intramolecular allylation of a (Z)-allylsilane onto an aldehyde under Brønsted acid activation. Complete 1,4-stereoinduction accounts for the formation of only two out of the possible four THP products. The level of 1,3-stereoinduction is optimal when the reaction is carried out in an apolar solvent, which is in accord with electrostatics being key to controlling this aspect of the stereoselectivity.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 1523-7060
Last Modified: 04 Jun 2017 04:59
URI: http://orca-mwe.cf.ac.uk/id/eprint/47239

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