Reaction of 1O2 with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides

P. H. Dussault; U. R. Zope

doi:10.1016/0040-4039(95)00231-Z

Reaction of ¹O₂ with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides

P. H. Dussault, U. R. Zope

Chemistry

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

17 Scopus citations

Abstract

The reaction of ¹O₂ with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

Original language	English (US)
Pages (from-to)	2187-2190
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	13
DOIs	https://doi.org/10.1016/0040-4039(95)00231-Z
State	Published - Mar 27 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Reaction of 1O2 with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides",

abstract = "The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.",

author = "Dussault, {P. H.} and Zope, {U. R.}",

note = "Funding Information: Acknowledgment: We are grateful to the American Cancer Society (CN-34) for support of this research. The NMR facility was partially purchased with NIH funding (SIG-1-S10-RR06301) and we thank Prof. Richard Shoemaker for valuable assistance with nOe experiments. We thank Mr. Richard Lee for his contributions to the characterization of la and lb.",

year = "1995",

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doi = "10.1016/0040-4039(95)00231-Z",

language = "English (US)",

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pages = "2187--2190",

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T1 - Reaction of 1O2 with alkoxyallylstannanes

T2 - Synthesis of 1,2-dioxolanes and allyl hydroperoxides

AU - Dussault, P. H.

AU - Zope, U. R.

N1 - Funding Information: Acknowledgment: We are grateful to the American Cancer Society (CN-34) for support of this research. The NMR facility was partially purchased with NIH funding (SIG-1-S10-RR06301) and we thank Prof. Richard Shoemaker for valuable assistance with nOe experiments. We thank Mr. Richard Lee for his contributions to the characterization of la and lb.

PY - 1995/3/27

Y1 - 1995/3/27

N2 - The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

AB - The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

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Reaction of ¹O₂ with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides

Abstract

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