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Convenient synthesis of highly optically active 2,3,4,6-tetrasubstituted tetrahydropyrans via Prins cyclization reaction (PCR) of optically active homoallylic alcohols with aldehydes
Authors:Kazuhide Kataoka
Affiliation:Department of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Okayama 700-0005, Japan
Abstract:Prins cyclization reaction (PCR) of optically active homoallylic alcohols, RaC*H(OH)CH2CHdouble bond; length as m-dashCHCH3 (1-substituted but-2-en-1-ol), with aldehydes (RbCHO) in the presence of an acid-catalyst (HX) affords (2-Rb,3-CH3,4-X,6-Ra)-tetrasubstituted tetrahydropyrans highly stereoselectively in good yields.
Keywords:Prins cyclization reaction   Enantiomeric excess   Nucleophile
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