Literature DB >> 18393515

Pd-catalyzed carboetherification of beta,gamma-unsaturated oximes: a novel approach to Delta2-isoxazolines.

Dahong Jiang1, Jinsong Peng, Yuanwei Chen.   

Abstract

A novel route to the synthesis of Delta2-isoxazoline derivatives is described. Reaction of beta,gamma-unsaturated oximes with aryl bromides via palladium-catalyzed carboetherification affords 3,5-disubstituted Delta2-isoxazolines in good yields. The use of Xantphos as ligand is crucial for the transformation. The carboetherification products can be further converted to beta-hydroxy ketones in the presence of Fe powder and NH4Cl.

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Year:  2008        PMID: 18393515     DOI: 10.1021/ol8002173

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  An expedient reductive method for conversion of ketoximes to the corresponding carbonyl compounds.

Authors:  Max M Majireck; Jason A Witek; Steven M Weinreb
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

2.  Gold redox catalysis for cyclization/arylation of allylic oximes: synthesis of isoxazoline derivatives.

Authors:  Abiola Azeez Jimoh; Seyedmorteza Hosseyni; Xiaohan Ye; Lukasz Wojtas; Yong Hu; Xiaodong Shi
Journal:  Chem Commun (Camb)       Date:  2019-07-09       Impact factor: 6.222

3.  Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors:  John P Wolfe
Journal:  Synlett       Date:  2006-11-13       Impact factor: 2.454

4.  Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores.

Authors:  Sang Won Park; Soong-Hyun Kim; Jaeyoung Song; Ga Young Park; Darong Kim; Tae-Gyu Nam; Ki Bum Hong
Journal:  Beilstein J Org Chem       Date:  2018-05-11       Impact factor: 2.883

5.  Unexpected Vulnerability of DPEphos to C-O Activation in the Presence of Nucleophilic Metal Hydrides.

Authors:  Mateusz K Cybulski; Nicholas A Beattie; Stuart A Macgregor; Mary F Mahon; Michael K Whittlesey
Journal:  Chemistry       Date:  2020-07-28       Impact factor: 5.236

Review 6.  Oxime radicals: generation, properties and application in organic synthesis.

Authors:  Igor B Krylov; Stanislav A Paveliev; Alexander S Budnikov; Alexander O Terent'ev
Journal:  Beilstein J Org Chem       Date:  2020-06-05       Impact factor: 2.883

7.  [2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: a general and practical access to isoxazolines.

Authors:  Liang Ma; Feng Jin; Xionglve Cheng; Suyan Tao; Gangzhong Jiang; Xingxing Li; Jinwei Yang; Xiaoguang Bao; Xiaobing Wan
Journal:  Chem Sci       Date:  2021-06-22       Impact factor: 9.825

  7 in total

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