Abstract
Abstract An enantioselective synthesis of substituted 2-aminotetralins from dihydronaphthalenes in four steps is described. The key step is the Jacobsen’s (diimine)copper-catalyzed asymmetric aziridination of dihydronaphthalenes to the respective aziridines in 33–82% yields and 60–87% enantiomeric excess. The enantioselectivity and the yield were dependent on the properties of the nitrene precursor. p Ts NIPh appeared in general to give better results than p NsN IPh. Aziridines were ring-opened in the benzylic position by catalytic hydrogenolysis in quantitative yields, and deprotected in two steps to the respective 2-aminotetralins in 66–85% yields. The synthesis of ( S )-2-aminotetralin (>98% ee) and ( S )-2-amino-7-methoxytetralin (56% ee) were accomplished in 30 and 52% overall yields, respectively.
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