First attempts at differential diastereoselection in catalytic reactions of N-chirally substituted dirhodium(ii) tetrakis[methyl 2-oxoimidazolidine-4(S)-carboxylates] with diazoacetates View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2001-11

AUTHORS

M. P. Doyle, D. J. Timmons, M. M. R. Arndt, A. Duursma, J. T. Colyer, H. Brünner

ABSTRACT

Chiral attachments on 2-oxoimidazolidine-4(S)-carboxylate ligands for dirhodium(ii) can provide differential diastereoselection in catalytic reactions of diazo compounds. The synthesis of these heterocyclic ligands from the readily available amino acid asparagine is reported. Reactions with diazoacetates offering intramolecular carbon—hydrogen insertion provide evaluative data that demonstrate differential diastereoselection. Surprisingly, placement of a carbonyl group within the chiral attachment removes enantiocontrol from the catalyst, presumably because of intramolecular ylide formation. More... »

PAGES

2156-2161

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1015061620557

DOI

http://dx.doi.org/10.1023/a:1015061620557

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1013469636


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