Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction.

Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction. Research Abstract Details 

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Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction. Abstract Text:

Brian M Cochran,Forrest E Michael,Brian M Cochran,Forrest E Michael,Brian M Cochran,Forrest E Michael,

A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A1,3 strain.

Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction. Publishing Authors By Initials

BM Cochran,FE Michael,BM Cochran,FE Michael,BM Cochran,FE Michael,

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Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Organic letters

VOLUME: 10

Page Numbers: 329-32

Journal Abbreviation: Org. Lett.

ISSN: 1523-7060

DAY: 22

MONTH: 12

YEAR: 2007

Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction. Information

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LANGUAGE: eng

NlmUniqueID: 100890393

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Grant and Affiliation Information for Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction.

AFFILIATION: Department of Chemistry, University of Washington, Box 351700, Seattle, Washington 98195-1700.

Country: United States

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MEDLINETA: Org Lett

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