Preparation of enantioselective enriched α-(dialkoxyphosphoryl) lactams via intramolecular C-H insertion with chiral dirhodium(II) catalysts

Pedro M. Pedro, Nuno R. Candeias, Carlos A.M. Afonso

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27 Citations (Scopus)

Abstract

The intramolecular C-H insertion on alpha-diazoacetamides is an extremely useful procedure for the preparation of a wide variety of heterocyclic compounds. In this work is presented a strategy for the preparation of enantioselective enriched alpha-(dialkoxyphosphoryl)lactams via dirhodium(II) catalyzed C-H insertion on alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides, in which enantiomeric excess up to 40% is reported. Moreover, a systematic study was undertaken on the chiral dirhodium(II) catalyst and the alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides influence on enantioselectivity. (C) 2004 Elsevier B.V. All rights reserved.
Original languageEnglish
Pages (from-to)17-24
Number of pages8
JournalJournal Of Molecular Catalysis A-Chemical
Volume227
Issue number1-2
DOIs
Publication statusPublished - 1 Mar 2005

Keywords

  • Phosphonates
  • Rhodium catalysts
  • CH insertion
  • Diazo compounds
  • Lactams

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