Synfacts 2007(9): 0943-0943  
DOI: 10.1055/s-2007-968843
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Diamination of Olefins

Contributor(s): Mark Lautens, Praew Thansandote
H. Du, W. Yuan, B. Zhao, Y. Shi*
Colorado State University, Fort Collins, USA
Further Information

Publication History

Publication Date:
23 August 2007 (online)


Complementary to previous approaches to diaminate olefins and as an extension to the group’s previous work in the area (H. Du, B. Zhao, Y. Shi J. Am. Chem. Soc. 2007, 129, 762), terminal olefins were diaminated at allylic and homoallylic carbons by a Pd-catalyzed C-H insertion under solvent-free conditions. The nitrogen source is di-tert-butyldiaziridinone, which can be synthesized in a few steps. The scope encompasses both monosubstituted and 1,1-disubstituted terminal olefins, and the resulting products can be converted into the free diamine by treatment with TFA and concentrated acid. Diamination is also possible, with 1,9-decadiene producing a 1:1 mixture of diastereomers and with 1,7-octadiene producing a single diastereomer.