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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	5386-5389
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	20
DOIs	https://doi.org/10.1021/ol502599r
Publication status	Published - 17 Oct 2014
Externally published	Yes

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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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doi = "10.1021/ol502599r",

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AU - Han, Songzhe

AU - Zard, Samir Z.

PY - 2014/10/17

Y1 - 2014/10/17

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.

U2 - 10.1021/ol502599r

DO - 10.1021/ol502599r

M3 - Article

AN - SCOPUS:84907963254

SN - 1523-7060

VL - 16

SP - 5386

EP - 5389

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

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

Abstract

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