Literature DB >> 12443064

O-alkenyl hydroxylamines: a new concept for cyclofunctionalization.

Roderick W Bates1, Kanicha Sa-Ei.   

Abstract

[reaction: see text] Treatment of O-homoallylhydroxylamines with palladium(II) and copper(II) in the presence of a base, methanol, and carbon monoxide results in the formation of isooxazolidines. An electron-withdrawing group on the hydroxylamine nitrogen is essential. When carbamate groups are used the products are formed exclusively as their cis isomers.

Entities:  

Year:  2002        PMID: 12443064     DOI: 10.1021/ol026701d

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


  4 in total

1.  Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation.

Authors:  Shuklendu D Karyakarte; Thomas P Smith; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-08-15       Impact factor: 4.354

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.  Influence of hydroxylamine conformation on stereocontrol in Pd-catalyzed isoxazolidine-forming reactions.

Authors:  Georgia S Lemen; Natalie C Giampietro; Michael B Hay; John P Wolfe
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

4.  Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.

Authors:  Zainab M Khoder; Christina E Wong; Sherry R Chemler
Journal:  ACS Catal       Date:  2017-06-15       Impact factor: 13.084

  4 in total

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