Chiral N-Heterocyclic Carbene−Pd(0)-Catalyzed Asymmetric Diamination of Conjugated Dienes and Triene

• Published in: Journal of organic chemistry Vol. 73; no. 2; pp. 749 - 751
• Main Authors: Xu, Liang, Shi, Yian
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 18.01.2008
• Subjects: Alkenes - chemistry; Amination; Aziridines - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic Compounds - chemistry; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Hydrocarbons - chemistry; Ketones - chemical synthesis; Ketones - chemistry; Methane - analogs & derivatives; Methane - chemistry; Molecular Structure; Organic chemistry; Palladium - chemistry; Preparations and properties; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Catalytic reaction; Trienic compound; Enantioselectivity; Regioselectivity; Nitrogen heterocycle; Palladium complex; Chiral compound; Diastereoselectivity; Carbene; Amination; Asymmetric synthesis; Conjugated dienic compound; Enantiomeric excess; Catalyst
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo702167u

Studies show that a variety of conjugated dienes and triene can be enantioselectively diaminated using di-tert-butyldiaziridinone as nitrogen source and chiral N-heterocyclic carbene−Pd(0) complex as catalyst in good enantioselectivity (62−91% ee) with high regio- and diastereoselectivity.