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

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 encouragi...