Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes

Patrick H. Dussault; Tony K. Trullinger; Farhana Noor-e-Ain

doi:10.1021/ol0265259

Opening of Substituted Oxetanes with H₂O₂ and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes

Patrick H. Dussault, Tony K. Trullinger, Farhana Noor-e-Ain

Chemistry

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

75 Scopus citations

Abstract

(Equation Presented) Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.

Original language	English (US)
Pages (from-to)	4591-4593
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	26
DOIs	https://doi.org/10.1021/ol0265259
State	Published - Dec 26 2002

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes",

abstract = "(Equation Presented) Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.",

author = "Dussault, {Patrick H.} and Trullinger, {Tony K.} and Farhana Noor-e-Ain",

year = "2002",

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doi = "10.1021/ol0265259",

language = "English (US)",

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T2 - Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes

AU - Dussault, Patrick H.

AU - Trullinger, Tony K.

AU - Noor-e-Ain, Farhana

PY - 2002/12/26

Y1 - 2002/12/26

N2 - (Equation Presented) Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.

AB - (Equation Presented) Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.

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Opening of Substituted Oxetanes with H₂O₂ and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes

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