Literature DB >> 24939636

Catalytic intermolecular alkene oxyamination with nitrenes.

Geoffroy Dequirez1, Jennifer Ciesielski, Pascal Retailleau, Philippe Dauban.   

Abstract

The Rh(II)-catalyzed intermolecular addition of nitrenes to aromatic and aliphatic alkenes provides vicinal amino alcohols with yields of up to 95 % and complete regioselectivity. This 1,2-oxyamination reaction involves the formation of an aziridine intermediate that undergoes in situ ring opening. The latter is induced by the Rh-bound nitrene that behaves as a Lewis acid.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; aminohydroxylation; nitrenes; rhodium; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 24939636     DOI： 10.1002/chem.201400301

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  7 in total

1.  Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  ACS Catal       Date:  2019-09-24       Impact factor: 13.084

2.  Biomimetic 2-Imino-Nazarov Cyclizations via Eneallene Aziridination.

Authors:  Joshua R Corbin; Devin R Ketelboeter; Israel Fernández; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2020-03-10       Impact factor: 15.419

3.  Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

Authors:  Logan A Combee; Shea L Johnson; Julie E Laudenschlager; Michael K Hilinski
Journal:  Org Lett       Date:  2019-03-25       Impact factor: 6.005

4.  Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Authors:  Honghui Lei; John H Conway; Caleb C Cook; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-07-16       Impact factor: 15.419

5.  Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex.

Authors:  Finn Burg; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-10-20       Impact factor: 15.419

6.  Intramolecular N-Me and N-H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles.

Authors:  Mahesh P Paudyal; Mingliang Wang; Juha H Siitonen; Yimin Hu; Muhammed Yousufuddin; Hong C Shen; John R Falck; László Kürti
Journal:  Org Biomol Chem       Date:  2021-01-28       Impact factor: 3.876

7.  Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.

Authors:  Deng-Fu Lu; Cheng-Liang Zhu; Zhen-Xin Jia; Hao Xu
Journal:  J Am Chem Soc       Date:  2014-09-16       Impact factor: 15.419
  7 in total

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