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Generally Applicable Organocatalytic Tetrahydropyranylation of Hydroxy Functionalities with Very Low Catalyst Loading

Mike Kotke, Peter R. Schreiner*

*Institute of Organic Chemistry, Justus-Liebig University Gießen, Heinrich-Buff-Ring 58, 35392 Gießen, Germany, Email:

M. Kotke, P. R. Schreiner, Synthesis, 2007, 779-790.

DOI: 10.1055/s-2007-965917

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A N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea-catalyzed tetrahydropyran and 2-methoxypropene protection of hydroxyl groups is broadly applicable to sterically hindered and acid-sensitive substrates. A mechanistic interpretation of the high catalytic efficiency is given.

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Key Words

acetals, alcohols, organocatalysis, protecting groups, tetrahydropyranylation, supported catalysis

ID: J66-Y2007-0910