Catalytic Asymmetric Synthesis of Cyclic Sulfamides from Conjugated Dienes

This paper describes the catalytic asymmetric diamination of alkyl dienes using N,N′-di-tert-butylthiadiaziridine 1,1-dioxide in the presence of Pd(0) and a chiral phosphoramidite ligand to give cyclic sulfamides in high yield and high ee. The diamination is also amenable to gram scale.

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 4; pp. 796 - 799
Main Authors Cornwall, Richard G, Zhao, Baoguo, Shi, Yian
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.02.2013
Amer Chemical Soc
Subjects
Alkadienes - chemistry
Catalysis
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
ligands
Molecular Structure
organic compounds
Palladium - chemistry
Physical Sciences
Science & Technology
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
ALKENES
PROMOTED INTRAMOLECULAR DIAMINATION
ELECTROPHILIC DIAMINATION
MECHANISTIC PATHWAYS
CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION
OXIDATIVE DIAMINATION
DIALKYLZINC REAGENTS
INHIBITORS
INTERMOLECULAR DIAMINATION
VICINAL DIAMINATION
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Summary:This paper describes the catalytic asymmetric diamination of alkyl dienes using N,N′-di-tert-butylthiadiaziridine 1,1-dioxide in the presence of Pd(0) and a chiral phosphoramidite ligand to give cyclic sulfamides in high yield and high ee. The diamination is also amenable to gram scale.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol303469a