Rhodium(III)‐Catalyzed Oxidative Intramolecular 1,1‐Oxyamination of Alkenes with Protected Amino Acids to Produce Oxazoloisoindole‐2,5‐diones | Zendy

Takahashi Hiroto | Zendy; Nagashima Yuki | Zendy; Tanaka Ken | Zendy

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Rhodium(III)‐Catalyzed Oxidative Intramolecular 1,1‐Oxyamination of Alkenes with Protected Amino Acids to Produce Oxazoloisoindole‐2,5‐diones

Author(s) -

Takahashi Hiroto,

Nagashima Yuki,

Tanaka Ken

Publication year - 2021

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202100143

Subject(s) - chemistry , intramolecular force , rhodium , oxazolidine , oxidative phosphorylation , cyclopentadienyl complex , catalysis , bond cleavage , stereochemistry , medicinal chemistry , oxidative addition , alkene , amino acid , organic chemistry , biochemistry

It has been established that an electron‐deficient bis(ethoxycarbonyl)‐substituted cyclopentadienyl (Cp E ) rhodium(III) complex catalyzes the oxidative intramolecular 1,1‐oxyamination of alkenes with N ‐benzoyl amino acids to produce oxazoloisoindole‐2,5‐diones. Experimental and theoretical mechanistic studies revealed that this oxidative 1,1‐oxyamination proceeds via not the aza‐Wacker reaction but the formation of a rhoda(III)oxazolidine initiated by the carboxylic acid‐directed N−H bond cleavage.

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