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Rh(III)-Catalyzed Stereoselective C-C Bond Cleavage of ACPs with N-Phenoxyacetamides: The Critical Role of the Nucleophilic Directing Group.
Singh, Anurag; Dey, Arnab; Volla, Chandra M R.
Afiliação
  • Singh A; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
  • Dey A; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
  • Volla CMR; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
J Org Chem ; 86(15): 10474-10483, 2021 Aug 06.
Article em En | MEDLINE | ID: mdl-34296871
Rh(III)-catalyzed redox-neutral chemodivergent coupling of N-phenoxyacetamides and alkylidenecyclopropanes (ACPs) has been documented. The reaction proceeds via C-H activation, regioselective migratory insertion and stereoselective ß-carbon elimination followed by ß-hydride elimination, resulting in o-dienylation of phenols in nonpolar solvents, whereas [3 + 2]-annulation leading to dihydrobenzofurans was realized in polar fluorinated solvents. It was observed that the nucleophilic directing group controls the elimination of ß-carbon and so plays a vital role for achieving high stereoselectivities. The synthetic utility of the dienylation and annulation was demonstrated by carrying out gram scale reactions and further derivatization.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article