Practical one-pot stereospecific preparation of vicinal and 1,3-diols

Bjorn Bohman; Gavin R. Flematti; C. Rikard Unelius

doi:10.1016/j.tetlet.2016.11.101

Practical one-pot stereospecific preparation of vicinal and 1,3-diols

Bjorn Bohman, Gavin R. Flematti, C. Rikard Unelius

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from commercially 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.

Original language	English
Pages (from-to)	75-77
Number of pages	3
Journal	Tetrahedron Letters
Volume	58
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2016.11.101
Publication status	Published - 4 Jan 2017

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10.1016/j.tetlet.2016.11.101

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title = "Practical one-pot stereospecific preparation of vicinal and 1,3-diols",

abstract = "A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from commercially 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.",

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AU - Bohman, Bjorn

AU - Flematti, Gavin R.

AU - Unelius, C. Rikard

PY - 2017/1/4

Y1 - 2017/1/4

N2 - A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from commercially 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.

AB - A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from commercially 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.

KW - Acetals

KW - DIBALH

KW - Diols

KW - Grignard

KW - Pheromone

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JO - Tetrahedron Letters

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Practical one-pot stereospecific preparation of vicinal and 1,3-diols

Abstract

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Discovery of Signalling Molecules that Mediate Communication in the Environment

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Practical one-pot stereospecific preparation of vicinal and 1,3-diols

Abstract

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Discovery of Signalling Molecules that Mediate Communication in the Environment

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