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Literature DB >> 22242841

Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes.

Colombe Gronnier¹, Søren Kramer, Yann Odabachian, Fabien Gagosz.

Abstract

In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.

Entities: Chemical

Year: 2011 PMID： 22242841 DOI： 10.1021/ja209866a

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

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Cited

8 in total

1. Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

Authors: Yujing Zhou; Lin Zhou; Luke T Jesikiewicz; Peng Liu; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2020-05-19 Impact factor: 15.419

2. Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.

Authors: Owen A Davis; James A Bull
Journal: Angew Chem Int Ed Engl Date: 2014-10-14 Impact factor: 15.336

3. Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives.

Authors: Peng-Hua Li; Jin-Ming Yang; Yin Wei; Min Shi
Journal: ChemistryOpen Date: 2016-12-13 Impact factor: 2.911

4. Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp³)-C(sp³) bond cleavage.

Authors: Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal: Chem Sci Date: 2017-01-23 Impact factor: 9.825

Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes.

1. Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

2. Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.

3. Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives.

4. Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp³)-C(sp³) bond cleavage.

Review 5. Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances.

6. 3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.

7. Crystal structure of 3-bromo-pyridine N-oxide.

Review 8. Preparation and Uses of Chlorinated Glycerol Derivatives.

Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes.

1. Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

2. Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.

3. Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives.

4. Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.

Review 5. Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances.

6. 3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.

7. Crystal structure of 3-bromo-pyridine N-oxide.

Review 8. Preparation and Uses of Chlorinated Glycerol Derivatives.

4. Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp³)-C(sp³) bond cleavage.