Catalytic Asymmetric Allylic and Homoallylic Diamination of Terminal Olefins via Formal C−H Activation

This paper describes a catalytic asymmetric diamination process for terminal olefins at allylic and homoallylic carbons via formal C−H activation using di-tert-butyldiaziridinone as nitrogen source with a catalyst generated from Pd2(dba)3 and chiral phosphorus amidite ligand. A wide variety of readi...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 130; no. 27; pp. 8590 - 8591
Main Authors Du, Haifeng, Zhao, Baoguo, Shi, Yian
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.07.2008
Amer Chemical Soc
Subjects
Alkenes - chemistry
Aziridines - chemistry
Carbon - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Diamines - chemical synthesis
Diamines - chemistry
Hydrogen - chemistry
Ligands
Molecular Structure
Naphthalenes - chemistry
Nitrogen - chemistry
Organometallic Compounds - chemistry
Phosphorus - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
ALKENES
DIENES
PROMOTED INTRAMOLECULAR DIAMINATION
ELECTROPHILIC DIAMINATION
DIETHYLZINC
ENANTIOSELECTIVE CONJUGATE ADDITION
COMPLEXES
DIALKYLZINC REAGENTS
VICINAL DIAMINATION
1,2-DIAMINATION
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Summary:This paper describes a catalytic asymmetric diamination process for terminal olefins at allylic and homoallylic carbons via formal C−H activation using di-tert-butyldiaziridinone as nitrogen source with a catalyst generated from Pd2(dba)3 and chiral phosphorus amidite ligand. A wide variety of readily available terminal olefins can be effectively diaminated in good yields with high regio-, diastereo-, and enantioselectivities.
Bibliography:istex:9B3E32DFF3F8A1112E61EC024BE18CE1FC463157
ark:/67375/TPS-CLH5SPD6-7
Experimental procedures, ligand studies, characterizations, X-ray structures of L1, L2, and 6, and data for determination of enantiomeric excess of diamination products along with the NMR spectra of compounds. This material is available free of charge via the Internet at http://pubs.acs.org.
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NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja8027394