Dispiroketals in Synthesis (Part 19): Dispiroketals as Enantioselective and Regioselective Protective Agents for Symmetric Cyclic and Acyclic Polyols.

DOI: 10.1016/0957-4166(95)00318-J

Source and publish data:

Tetrahedron Asymmetry p. 2403 - 2440 (1995)

Update date:2022-08-05

Topics:

Authors:

Downham, Robert

Edwards, Paul J.

Entwistle, David A.

Hughes, Andrew B.

Kim, Kun Soo

Ley, Steven V.

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Article abstract of DOI:10.1016/0957-4166(95)00318-J

The enantioselective preparation of both enantiomers of a C₂-symmetric diphenyl-bidihydropyran 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.

Full text of DOI:10.1016/0957-4166(95)00318-J

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