title: 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 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 bocks for polypropionate synthesis.
authors.affiliation: Department of Chemistry, University of Puerto Rico, Río Piedras Campus, PO Box 23346, San Juan, P.R. 00932-3346, USA.
authors.forename: Wildeliz
authors.initials: W
authors.lastname: Torres
authors.forename: Gerardo
authors.initials: G
authors.lastname: Torres
authors.forename: José A
authors.initials: JA
authors.lastname: Prieto
keywords: 3, 4-epoxy alcohols; aluminum; cleavage; epoxides; stereotetrads