Hydroperoxide-mediated CC bond formation: Synthesis of 1,2-dioxolanes from alkoxyhydroperoxides in the presence of Lewis acids

Patrick H. Dussault; Umesh Zope

doi:10.1016/0040-4039(95)00622-J

Hydroperoxide-mediated CC bond formation: Synthesis of 1,2-dioxolanes from alkoxyhydroperoxides in the presence of Lewis acids

Patrick H. Dussault, Umesh Zope

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Abstract

Lewis-acid activation of ozonolysis-derived hydroperoxyketals affords intermediate hydroperoxycarbenium ions (protonated carbonyl oxides) which undergo addition of allyltrimethylsilane to directly afford 1,2-dioxolanes.

Original language	English (US)
Pages (from-to)	3655-3658
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	21
DOIs	https://doi.org/10.1016/0040-4039(95)00622-J
State	Published - May 22 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)00622-J

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title = "Hydroperoxide-mediated CC bond formation: Synthesis of 1,2-dioxolanes from alkoxyhydroperoxides in the presence of Lewis acids",

abstract = "Lewis-acid activation of ozonolysis-derived hydroperoxyketals affords intermediate hydroperoxycarbenium ions (protonated carbonyl oxides) which undergo addition of allyltrimethylsilane to directly afford 1,2-dioxolanes.",

author = "Dussault, {Patrick H.} and Umesh Zope",

note = "Funding Information: Acknowledgment. This work was supported by the National Institutes of Health (GM45571)",

year = "1995",

month = may,

day = "22",

doi = "10.1016/0040-4039(95)00622-J",

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journal = "Tetrahedron Letters",

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T1 - Hydroperoxide-mediated CC bond formation

T2 - Synthesis of 1,2-dioxolanes from alkoxyhydroperoxides in the presence of Lewis acids

AU - Dussault, Patrick H.

AU - Zope, Umesh

N1 - Funding Information: Acknowledgment. This work was supported by the National Institutes of Health (GM45571)

PY - 1995/5/22

Y1 - 1995/5/22

N2 - Lewis-acid activation of ozonolysis-derived hydroperoxyketals affords intermediate hydroperoxycarbenium ions (protonated carbonyl oxides) which undergo addition of allyltrimethylsilane to directly afford 1,2-dioxolanes.

AB - Lewis-acid activation of ozonolysis-derived hydroperoxyketals affords intermediate hydroperoxycarbenium ions (protonated carbonyl oxides) which undergo addition of allyltrimethylsilane to directly afford 1,2-dioxolanes.

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U2 - 10.1016/0040-4039(95)00622-J

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Hydroperoxide-mediated CC bond formation: Synthesis of 1,2-dioxolanes from alkoxyhydroperoxides in the presence of Lewis acids

Abstract

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