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LEWIS ACID CATALYZED FORMATION OF TETRAHYDROPYRANS IN IONIC LIQUID
Citation:
Li, C. J., C. K. Keh, R S. Varma*, AND V Namboodiri**. LEWIS ACID CATALYZED FORMATION OF TETRAHYDROPYRANS IN IONIC LIQUID. Presented at 223rd American Chemical Society National Meeting, Orlando, FL, 4/7-11/2002.
Description:
Tetrahydropyrans are integral moieties in innumerable natural products and have inspired the development of a variety of different methodologies. A Prins-type cyclization involving the coupling of a homoallylic alcohol and an aldehyde in the presence of catalytic scandium triflate in ionic liquid was developed. The ionic liquid of choice for this reaction is 1-butyl-3-methylimidazoliumhexafluorphosphate ([bmim]PF6). A variety of different aldehydes were reacted to yield tetrahydropyranols in moderate to good yields. This methodology was extended to form trans-fused tetrahydropyran rings.