DISPIROKETALS IN SYNTHESIS .19. DISPIROKETALS AS ENANTIOSELECTIVE AND REGIOSELECTIVE PROTECTIVE AGENTS FOR SYMMETRICAL CYCLIC AND ACYCLIC POLYOLS

The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmet...

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Published inTetrahedron: asymmetry Vol. 6; no. 10; pp. 2403 - 2440
Main Authors DOWNHAM, R, EDWARDS, PJ, ENTWISTLE, DA, HUGHES, AB, KIM, KS, LEY, SV
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.10.1995
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CHAIN
KETONES
CONDURITOL-B
REDUCTION
CATALYST
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Summary:The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.
ISSN:0957-4166
DOI:10.1016/0957-4166(95)00318-J