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

70 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

Access to Document

10.1021/ol0265259

Fingerprint Dive into the research topics of 'Opening of Substituted Oxetanes with H<sub>2</sub>O<sub>2</sub> and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes'. Together they form a unique fingerprint.

Cite this

@article{45fc8396ec7642f09c91fb113fa841b9,

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",

month = dec,

day = "26",

doi = "10.1021/ol0265259",

language = "English (US)",

volume = "4",

pages = "4591--4593",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

T1 - Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides

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.

UR - http://www.scopus.com/inward/record.url?scp=0442268762&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0442268762&partnerID=8YFLogxK

U2 - 10.1021/ol0265259

DO - 10.1021/ol0265259

M3 - Article

C2 - 12489937

AN - SCOPUS:0442268762

VL - 4

SP - 4591

EP - 4593

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 26

ER -