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

Wildeliz Torres; Gerardo Torres; José A. Prieto

doi:10.1055/s-0032-1317316

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(17): 2534-2538
DOI: 10.1055/s-0032-1317316

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

Wildeliz Torres

Department of Chemistry, University of Puerto Rico, Río Piedras Campus, PO Box 23346, San Juan, P.R. 00932-3346, USA Fax: +1(787)7596885 eMail: jose.prieto2@upr.edu

,

Gerardo Torres

Department of Chemistry, University of Puerto Rico, Río Piedras Campus, PO Box 23346, San Juan, P.R. 00932-3346, USA Fax: +1(787)7596885 eMail: jose.prieto2@upr.edu

,

José A. Prieto*

Department of Chemistry, University of Puerto Rico, Río Piedras Campus, PO Box 23346, San Juan, P.R. 00932-3346, USA Fax: +1(787)7596885 eMail: jose.prieto2@upr.edu

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Abstract

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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.

Key words

cleavage - epoxides - aluminum - stereotetrads - 3,4-epoxy alcohols

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Referenzen

References and Notes
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Zusatzmaterial

Supporting Information