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Highly ?-selective hydrolysis of ?,?-epoxyalcohols using tetrabutylammonium fluoride.

ABSTRACT: We report a simple method for the highly regio- and stereoselective hydrolysis of ?,?-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored ?-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).

SUBMITTER: Mukerjee P

PROVIDER: S-EPMC2937070 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Highly α-selective hydrolysis of α,β-epoxyalcohols using tetrabutylammonium fluoride.

Mukerjee Purba P Abid Mohammed M Schroeder Frank C FC

Organic letters 20100901 18

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/H(2)O 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 hydr ...[more]

PMID: 20722386

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