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

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

Research output: Contribution to journalArticleScientificpeer-review

29 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
Externally publishedYes
Publication typeA1 Journal article-refereed

Keywords

  • phosphonates
  • diazo compounds
  • rhodium catalysts
  • C-H insertion
  • lactams
  • ALPHA-DIAZOACETAMIDES
  • STEREOCONTROL
  • REGIOCONTROL

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