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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.