Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines

• Kebin Mao,
• Guoqin Fan,
• Yuanhong Liu,
• Shi Li,
• Xu You and
• Dan Liu

Beilstein J. Org. Chem. 2013, 9, 621–627, doi:10.3762/bjoc.9.69

• Chemical Technology, Shenyang 110142, People’s Republic of China 10.3762/bjoc.9.69 Abstract Low-valency titanium species, generated in situ by using Ti(OiPr)4/2 c-C5H9MgCl reagent, react with imines to give a titanium-imine complex that can couple with terminal alkynes to provide azatitanacyclopentenes

• undergoes an unexpected 1,3-amino migration on silica gel during the column chromatography. Keywords: allylic amine; azatitanacyclopentene; reductive cross-coupling; regioselectivity; terminal alkyne; titanium-imine complex; Introduction Allylic amines are fundamental three-carbon building blocks in