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Stereoselective Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans Using an Intramolecular Allylation Strategy

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journal contribution
posted on 28.09.2006, 00:00 by Peter J. Jervis, Benson M. Kariuki, Liam R. Cox
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.