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Literature DB >> 21244004

Gold-catalyzed stereoselective synthesis of azacyclic compounds through a redox/[2 + 2 + 1] cycloaddition cascade of nitroalkyne substrates.

Appaso Mahadev Jadhav¹, Sabyasachi Bhunia, Hsin-Yi Liao, Rai-Shung Liu.

Abstract

We report a new redox/cycloaddition cascade on readily available 1-alkynyl-2-nitrobenzenes that produces complex azacyclic compounds stereoselectively. The core structures of the resulting products are constructed through a formal [2 + 2 + 1] cycloaddition among α-carbonyl carbenoids, nitroso species, and external alkenes.

Entities: Chemical

Year: 2011 PMID： 21244004 DOI： 10.1021/ja110514s

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

1. Umpolung reactivity of indole through gold catalysis.

Authors: Biao Lu; Yingdong Luo; Lianzhu Liu; Longwu Ye; Yanzhao Wang; Liming Zhang
Journal: Angew Chem Int Ed Engl Date: 2011-07-14 Impact factor: 15.336

2. Mechanism of gold(I)-catalyzed rearrangements of acetylenic amine-N-oxides: computational investigations lead to a new mechanism confirmed by experiment.

Authors: Elizabeth L Noey; Yingdong Luo; Liming Zhang; K N Houk
Journal: J Am Chem Soc Date: 2011-12-22 Impact factor: 15.419

3. [3,3]-Sigmatropic rearrangement versus carbene formation in gold-catalyzed transformations of alkynyl aryl sulfoxides: mechanistic studies and expanded reaction scope.

Authors: Biao Lu; Yuxue Li; Youliang Wang; Donald H Aue; Yingdong Luo; Liming Zhang
Journal: J Am Chem Soc Date: 2013-06-03 Impact factor: 15.419

Gold-catalyzed stereoselective synthesis of azacyclic compounds through a redox/[2 + 2 + 1] cycloaddition cascade of nitroalkyne substrates.

1. Umpolung reactivity of indole through gold catalysis.

2. Mechanism of gold(I)-catalyzed rearrangements of acetylenic amine-N-oxides: computational investigations lead to a new mechanism confirmed by experiment.

3. [3,3]-Sigmatropic rearrangement versus carbene formation in gold-catalyzed transformations of alkynyl aryl sulfoxides: mechanistic studies and expanded reaction scope.

4. Recent advances in the gold-catalyzed additions to C-C multiple bonds.

Review 5. Homogeneous Gold-Catalyzed Oxidation Reactions.

6. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

7. Intriguing mechanistic labyrinths in gold(I) catalysis.

8. Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts.