Stabilization of radicals by imides. A modular stereoselective approach to protected functional 1,2-diamines.

Abstract : Radical addition of various xanthates to N,N'-diacylimidazol-2-one occurs readily to give protected 1,2-diamines. The imide group stabilizes the adduct radical sufficiently to enable a second addition to unactivated alkenes. In some cases, the addition product could be converted into an indoline, a tetralone, or further added to an indole. Regioselective removal of one acyl group could also be accomplished.
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Submitted on : Monday, December 29, 2014 - 6:07:56 PM
Last modification on : Thursday, February 7, 2019 - 5:00:08 PM

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Songzhe Han, Samir Z Zard. Stabilization of radicals by imides. A modular stereoselective approach to protected functional 1,2-diamines.. Letters in Organic Chemistry, Bentham Science Publishers, 2014, 16 (20), pp.5386-5389. ⟨hal-01098821⟩

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