Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins

作者：Aaseng Jon Erik; Melnes Silje; Reian Gard; Gautun Odd R^*

来源：Tetrahedron, 2010, 66(52): 9790-9797.

DOI：10.1016/j.tet.2010.11.010

• N-(p-Toluenesulfonyl)iminophenyliodinane
• Dihydronaphthalenes
• Catalytic racemic aziridination
• Catalytic asymmetric aziridination
• 2-Aminotetralins

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. pTs=NIPh appeared in general to give better results than pNsN=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.

• 出版日期2010-12-24