Facile and Chemo-selective Cleavages of Allyl Ethers Utilizing Tetrabutylammonium Sulfate Radical Species

Seung Gak Yang; Min Young Park; Yong Hae Kim

doi:10.1055/s-2002-20475

LETTER

Facile and Chemo-selective Cleavages of Allyl Ethers Utilizing Tetrabutylammonium Sulfate Radical Species

Seung Gak Yang, Min Young Park, Yong Hae Kim*
Center for Molecular Design and Synthesis, Department of Chemistry, Korea Advanced Institute of Science and Technology, Taejon, 305-701, Korea
Fax: +82(42)8695818; e-Mail: kimyh@mail.kaist.ac.kr;

Abstract

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Abstract

Allyl ethers containing various functional groups reacted with tetrabutylammonium peroxydisulfate in acetonitrile under mild conditions to afford the corresponding cleaved alcohols in excellent yields.

Key words

cleavage of allyl ethers - tetrabutylammonium peroxydisulfate - chemo-selectivity - deprotection

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References

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The allyl ether containing aldehyde moiety 2m reacted with DIBAL-H (1 equiv) in the presence of NiCl₂[dppp] in the short reaction time (30 min) resulted in the corresponding alcohols as shown below (Equation 5).

Equation 5

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The aldehyde 4 was isolated (80%) and confirmed through GC analysis by comparison with the authentic sample of acrolein.