Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination

• Published in: Journal of organic chemistry Vol. 74; no. 21; pp. 8392 - 8395
• Main Authors: Zhao, Baoguo, Du, Haifeng, Shi, Yian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.11.2009; Amer Chemical Soc
• Subjects: Alkenes - chemistry; Amines - chemistry; Anions; Chemistry; Chemistry, Organic; Copper - chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; OXIDATION; ALKENES; PROMOTED INTRAMOLECULAR DIAMINATION; SIMMONS-SMITH CYCLOPROPANATION; ELECTROPHILIC DIAMINATION; CATALYZED DIAMINATION; METAL CATALYSIS; TERMINAL OLEFINS; VICINAL DIAMINATION; 1,2-DIAMINATION; Catalytic reaction; Copper Phosphates; Chiral compound; Copper complex; Dienic compound; Phosphorus Organic compounds; Anions; Olefin; Amination; Asymmetric synthesis; Organic phosphate; Copper I; Counter ion; Conjugated compound; Ethylenic compound
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/jo901685c

Various achiral and chiral Cu(I) salts have been prepared from mesitylcopper(I) and investigated for the diamination of conjugated olefins with 1,3-di-tert-butyldiaziridinone as nitrogen source. It has been found that copper(I) phosphate has high catalytic activity for the diamination, and encouraging ee’s have also been achieved with chiral phosphates as anionic counterions.