Novel Synthesis of 4,5-Unsubstituted 2,3-Dihydroisoxazoles from 5-Acetoxyisoxazolidines

Róbert Fischer; Daniela Lackovičová; Lubor Fišera

doi:10.1055/s-0032-1317682

Synthesis, Table of Contents

Synthesis 2012; 44(24): 3783-3788
DOI: 10.1055/s-0032-1317682

paper

Novel Synthesis of 4,5-Unsubstituted 2,3-Dihydroisoxazoles from 5-Acetoxyisoxazolidines

Róbert Fischer*

Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk

,

Daniela Lackovičová

Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk

,

Lubor Fišera

Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk

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Abstract

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Abstract

A new synthetic method for the preparation of 4,5-unsubstituted 2,3-dihydroisoxazoles from readily available 5-acetoxyisoxazolidines is presented. Elimination reactions are carried out in anhydrous N-methylpyrrolidin-2-one (NMP) with a catalytic amount of trimethylsilyl triflate in the presence of N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) and provide the 2,3-dihydroisoxazoles in very good yields. The nature of the silylating agent plays a very important role in elimination process. Anhydrous reaction conditions are required, while trimethylsilanol, the product of trimethylsilyl triflate and N,O-bis(trimethylsilyl)trifluoroacetamide hydrolysis, can initiate reactions leading to deacetylation, giving side products and thus decreasing the total yield of the elimination.

Key words

elimination - Lewis acids - cycloaddition - nitrones - 2,3-dihydroisoxazoles

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References

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