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

Songzhe Han; Samir Z. Zard

doi:10.1021/ol502599r

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

Songzhe Han
, Samir Z. Zard

Laboratoire de Synthèse Organique

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

22 Citations (Scopus)

Résumé

(Chemical Equation Presented) 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.

langue originale	Anglais
Pages (de - à)	5386-5389
Nombre de pages	4
journal	Organic Letters
Volume	16
Numéro de publication	20
Les DOIs	https://doi.org/10.1021/ol502599r
état	Publié - 17 oct. 2014
Modification externe	Oui

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10.1021/ol502599r

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

abstract = "(Chemical Equation Presented) 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.",

author = "Songzhe Han and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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pages = "5386--5389",

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AU - Zard, Samir Z.

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N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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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DO - 10.1021/ol502599r

M3 - Article

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SP - 5386

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JO - Organic Letters

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

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