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 language | English |
---|---|
Pages (from-to) | 17-24 |
Number of pages | 8 |
Journal | Journal of Molecular Catalysis A: Chemical |
Volume | 227 |
Issue number | 1-2 |
DOIs | |
Publication status | Published - 1 Mar 2005 |
Externally published | Yes |
Publication type | A1 Journal article-refereed |
Keywords
- phosphonates
- diazo compounds
- rhodium catalysts
- C-H insertion
- lactams
- ALPHA-DIAZOACETAMIDES
- STEREOCONTROL
- REGIOCONTROL