Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides.

Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides. Research Abstract Details 

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Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides. Abstract Text:

Hui Xiong,Jian Huang,Sunil K Ghosh,Richard P Hsung,

The first intramolecular [4 + 3] cycloaddition reaction using nitrogen-stabilized chiral oxyallyl cations that are tethered to furan or diene through the nitrogen atom is described here. Formation of these nitrogen-stabilized chiral oxyallyl cations is achieved by a chemoselective epoxidation of chiral allenamides via syringe pump addition of dimethyl dioxirane. The ensuing cycloaddition can be carried out with a range of different lengths for the tether, and high diastereoselectivities can be obtained when using chiral allenamides with shorter tethers.

Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides. Publishing Authors By Initials

H Xiong,J Huang,SK Ghosh,RP Hsung,

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Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 125

Page Numbers: 12694-5

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 22

MONTH: Oct

YEAR: 2003

Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation of N-tethered allenamides. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

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AFFILIATION: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

Country: United States

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MEDLINETA: J Am Chem Soc

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