Synthesis of Stereotetrads by Regioselective Cleavage of Diastereomeric MEM-Protected 2-Methyl-3,4-epoxy Alcohols with Diethylpropynyl Aluminum

Abstract The regioselectivity of the epoxide ring opening of 2-methyl-3,4-epoxy alcohols with diethylpropynylalane has been studied as a function of the C1 alcohol protecting group. An efficient selective method was developed using MEM as the protecting group. The reaction proceeded in a highly regi...

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Bibliographic Details
Published in:Synlett 2012-10, Vol.23 (17), p.2534-2538
Main Authors: Torres, Wildeliz, Torres, Gerardo, Prieto, José A.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
letter
Organic chemistry
Preparations and properties
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Summary:Abstract The regioselectivity of the epoxide ring opening of 2-methyl-3,4-epoxy alcohols with diethylpropynylalane has been studied as a function of the C1 alcohol protecting group. An efficient selective method was developed using MEM as the protecting group. The reaction proceeded in a highly regioselective manner providing the useful 1,3-diol motif. The undesired 1,4-diol product produced by some free alcohol diastereomers was not observed. This highly stereoselective method provides access to termini-differentiated stereotetrads, which are essential building blocks for polypropionate synthesis.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0032-1317316