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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| Published in | Organic letters Vol. 15; no. 4; pp. 796 - 799 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
15.02.2013
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | 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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| AbstractList | 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. 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.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. 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. |
| Author | Cornwall, Richard G Zhao, Baoguo Shi, Yian |
| AuthorAffiliation | Colorado State University |
| AuthorAffiliation_xml | – name: Colorado State University |
| Author_xml | – sequence: 1 givenname: Richard G surname: Cornwall fullname: Cornwall, Richard G – sequence: 2 givenname: Baoguo surname: Zhao fullname: Zhao, Baoguo – sequence: 3 givenname: Yian surname: Shi fullname: Shi, Yian email: yian@lamar.colostate.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23362985$$D View this record in MEDLINE/PubMed |
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| Keywords | 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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| Snippet | 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... 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... 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... 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... |
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| SubjectTerms | 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 |
| Title | Catalytic Asymmetric Synthesis of Cyclic Sulfamides from Conjugated Dienes |
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