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 Bronsted 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.
Original language | English |
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Pages (from-to) | 4649-4652 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 8 |
DOIs | |
Publication status | Published - 28 Sept 2006 |