Palladium-Catalyzed γ‑Selective Arylation of Zincated Boc-Allylamines

The regio- and diastereoselective arylation of Boc-protected allylamines was performed via a one-pot lithiation/transmetalation to zinc/cross-coupling sequence, through an appropriate choice of a phosphine ligand. A variety of γ-arylated products were obtained in moderate to good yield, and the prod...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 15; pp. 3998 - 4000
Main Authors Millet, Anthony, Baudoin, Olivier
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.08.2014
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
DEPROTONATION
ALLYLIC AMINES
ENANTIOSELECTIVE SYNTHESES
COORDINATION
ARYL
EQUIVALENTS
LITHIATION
PIPERIDINES
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Summary:The regio- and diastereoselective arylation of Boc-protected allylamines was performed via a one-pot lithiation/transmetalation to zinc/cross-coupling sequence, through an appropriate choice of a phosphine ligand. A variety of γ-arylated products were obtained in moderate to good yield, and the products could be directly transformed into valuable γ-arylamines and β-aryl aldehydes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol5018257