The Silylalkyne-Prins Cyclization: Stereoselective Synthesis of Tetra- and Pentasubstituted Halodihydropyrans
Organic Letters2006Vol. 8(8), pp. 1633–1636
Citations Over TimeTop 10% of 2006 papers
Abstract
[reaction: see text] A new type of Prins cyclization using silylated secondary homopropargylic alcohols and aldehydes yielding tetra- and pentasubstituted dihydropyrans is described. The presence of the trimethylsilyl group in the triple bond favors the Prins cyclization and minimizes the 2-oxonia-[3,3]-sigmatropic rearrangement as a competitive alternative pathway. Ab initio theoretical calculations of the species involved in the rearrangements support the proposed mechanism. The process is highly stereoselective, affording cis-dihydropyran as the only isomer.
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