Cu(I)-Catalyzed Cycloguanidination of Olefins

• Published in: Organic letters Vol. 10; no. 6; pp. 1087 - 1090
• Main Authors: Zhao, Baoguo, Du, Haifeng, Shi, Yian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.03.2008; Amer Chemical Soc
• Subjects: Alkenes - chemistry; Catalysis; Chemistry; Chemistry, Organic; Copper - chemistry; Cyclization; Guanidine - chemistry; Molecular Structure; Physical Sciences; Science & Technology; X-Ray Diffraction; ORGANIC-SYNTHESIS; ALKENES; PROMOTED INTRAMOLECULAR DIAMINATION; ELECTROPHILIC DIAMINATION; CYCLIZATION REACTIONS; ASYMMETRIC DIAMINATION; RADICAL CYCLIZATION; CONJUGATED DIENES; GUANIDINE; VICINAL DIAMINATION

This paper describes a novel cycloguanidination process using CuCl as catalyst and diaziridinimines as the nitrogen source. A variety of conjugated dienes, trienes, and terminal olefins can be effectively diaminated under mild reaction conditions. For dienes and trienes, the reaction occurs at the t...