Highly α-Selective Hydrolysis of α.β- Epoxyalcohols Using Tetrabutylammonium Fluoride

Purba Mukarjee; Abid Shaikh; Frank C. Schroeder

Highly α-Selective Hydrolysis of α.β- Epoxyalcohols Using Tetrabutylammonium Fluoride

Purba Mukarjee
, Abid Shaikh
, Frank C. Schroeder

Biochemistry, Chemistry & Physics

Cornell University

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

Abstract

We report a simple method for the highly regio- and stereoselective hydrolysis of α,β-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H2O resulted in exclusive ring opening at the normally disfavored α-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

Original language	American English
Journal	Organic Letters
Volume	12
State	Published - 2010

Disciplines

Chemistry

Keywords

Enantiopure epoxyalcohols
Sharpless epoxidation
α
β-epoxyalcohols

Cite this

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title = "Highly α-Selective Hydrolysis of α.β- Epoxyalcohols Using Tetrabutylammonium Fluoride",

abstract = "We report a simple method for the highly regio- and stereoselective hydrolysis of α,β-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H2O resulted in exclusive ring opening at the normally disfavored α-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).",

keywords = "Enantiopure epoxyalcohols, Sharpless epoxidation, α, β-epoxyalcohols",

author = "Purba Mukarjee and Abid Shaikh and Schroeder, \{Frank C.\}",

year = "2010",

language = "American English",

volume = "12",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Highly α-Selective Hydrolysis of α.β- Epoxyalcohols Using Tetrabutylammonium Fluoride

AU - Mukarjee, Purba

AU - Shaikh, Abid

AU - Schroeder, Frank C.

PY - 2010

Y1 - 2010

N2 - We report a simple method for the highly regio- and stereoselective hydrolysis of α,β-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H2O resulted in exclusive ring opening at the normally disfavored α-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

AB - We report a simple method for the highly regio- and stereoselective hydrolysis of α,β-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H2O resulted in exclusive ring opening at the normally disfavored α-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).

KW - Enantiopure epoxyalcohols

KW - Sharpless epoxidation

KW - α

KW - β-epoxyalcohols

UR - http://dx.doi.org/10.1021/ol1015306

M3 - Article

SN - 1523-7060

VL - 12

JO - Organic Letters

JF - Organic Letters

ER -

Highly α-Selective Hydrolysis of α.β- Epoxyalcohols Using Tetrabutylammonium Fluoride

Abstract

Disciplines

Keywords

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