Title of article
Regioselective cleavage of cis- and trans-2-methyl-3,4-epoxy alcohols with diethylpropynyl aluminum
Author/Authors
Tirado، نويسنده , , Raymond and Torres، نويسنده , , Gerardo and Torres، نويسنده , , Wildeliz and Prieto، نويسنده , , José A.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2005
Pages
5
From page
797
To page
801
Abstract
The regioselectivity of the reaction of diethylpropynyl aluminum with diastereomeric 2-methyl-3,4-epoxy alcohols was studied. The preferred side of attack (1,3-diol vs 1,4-diol product) depends on the stereochemical disposition of the substituents. NMR studies showed that the regiochemistry of this reaction is governed by the aluminum coordination pattern. Protection of the alcohol with MEM provides the 1,3-diol product in systems where the free alcohol produced the 1,4-diols.
Keywords
polypropionate synthesis , Epoxide cleavage , Alkynyl aluminum , Stereotetrads
Journal title
Tetrahedron Letters
Serial Year
2005
Journal title
Tetrahedron Letters
Record number
1844626
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