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Synlett 2012; 23(17): 2534-2538
DOI: 10.1055/s-0032-1317316
DOI: 10.1055/s-0032-1317316
letter
Synthesis of Stereotetrads by Regioselective Cleavage of Diastereomeric MEM-Protected 2-Methyl-3,4-epoxy Alcohols with Diethylpropynyl Aluminum
Further Information
Publication History
Received: 25 June 2012
Accepted after revision: 28 August 2012
Publication Date:
21 September 2012 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
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