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Synthesis of stereotetrads by regioselective cleavage of diastereomeric MEM-protected 2-methyl-3,4-epoxy alcohols with diethylpropynyl aluminum.
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ABSTRACT:
SUBMITTER: Torres W
PROVIDER: S-EPMC3806138 | biostudies-literature | 2012 Oct
REPOSITORIES: biostudies-literature
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Synthesis of stereotetrads by regioselective cleavage of diastereomeric MEM-protected 2-methyl-3,4-epoxy alcohols with diethylpropynyl aluminum.
Synlett : accounts and rapid communications in synthetic organic chemistry 20121001 17
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 ...[more]