Palladium-catalyzed ring-forming aminoacetoxylation of alkenes

Erik J. Alexanian; Chulbom Lee; Erik J. Sorensen

doi:10.1021/ja051406k

Palladium-catalyzed ring-forming aminoacetoxylation of alkenes

Erik J. Alexanian, Chulbom Lee, Erik J. Sorensen

Chemistry

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

372 Scopus citations

Abstract

A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)₂ as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes.

Original language	English (US)
Pages (from-to)	7690-7691
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	21
DOIs	https://doi.org/10.1021/ja051406k
State	Published - Jun 1 2005

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja051406k

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abstract = "A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)2 as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes.",

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AU - Lee, Chulbom

AU - Sorensen, Erik J.

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Y1 - 2005/6/1

N2 - A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)2 as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes.

AB - A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)2 as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

Palladium-catalyzed ring-forming aminoacetoxylation of alkenes

Abstract

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