Practical one-pot stereospecific preparation of vicinal and 1,3-diols
Date
2017
Authors
Bohman, Bjorn
Flematti, Gavin R.
Unelius, C. Rikard
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Abstract
A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from com-
mercially available enantiopure hydroxy esters has been developed. The esters were reduced with
DIBALH and alkylated in situ with 4-pentenylmagnesium bromide, which after workup generated the title
diols as diastereomeric pairs. These pairs were easily separated by preparative chromatography, affording
products with retained stereoisomeric purity from the starting materials. This method represents an
expedient preparation of many common natural products, such as cerambycid beetle pheromones and
intermediates towards bicyclic acetal bark beetle pheromones
Description
Keywords
Diols, DIBALH, Grignard, Acetals, Pheromone
Citation
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Source
Tetrahedron Letters
Type
Journal article
Book Title
Entity type
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License Rights
Restricted until
2099-12-31
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