Intramolecular reactions of hydroperoxides and oxetanes: Stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes

Peng Dai; Patrick H. Dussault

doi:10.1021/ol051407h

Intramolecular reactions of hydroperoxides and oxetanes: Stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes

Peng Dai, Patrick H. Dussault

Chemistry

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

52 Scopus citations

Abstract

(Chemical Equation Presented) The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.

Original language	English (US)
Pages (from-to)	4333-4335
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	20
DOIs	https://doi.org/10.1021/ol051407h
State	Published - Sep 29 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.",

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AU - Dussault, Patrick H.

PY - 2005/9/29

Y1 - 2005/9/29

N2 - (Chemical Equation Presented) The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.

AB - (Chemical Equation Presented) The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.

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Intramolecular reactions of hydroperoxides and oxetanes: Stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes

Abstract

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