Tetrahedron

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

JE Aaseng, S Melnes, G Reian, OR Gautun

Index: Aaseng, Jon Erik; Melnes, Silje; Reian, Gard; Gautun, Odd R. Tetrahedron, 2010 , vol. 66, # 52 p. 9790 - 9797

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Citation Number: 13

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. pTsNIPh appeared in general to ...

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