Journal
TETRAHEDRON LETTERS
Volume 46, Issue 5, Pages 797-801Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.12.018
Keywords
epoxide cleavage; alkynyl aluminum; stereotetrads; polypropionate synthesis
Categories
Ask authors/readers for more resources
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. (C) 2004 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available