Abstract
In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.
Original language | English |
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Pages (from-to) | 211-240 |
Number of pages | 30 |
Journal | Green Chemistry Letters and Reviews |
Volume | 5 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2012 |
Publication type | A1 Journal article-refereed |
Funding
We thank the Fundacaopara a Ciencia e Tecnologia (POCI 2010) and FEDER (SFRH/BPD/46589/2008, SFRH/BD/72376/2010 PTDC/QUI/66695/2006, PTDC/QUI/70383/2006) for financial support.
Keywords
- diazoacetamides
- C-H insertion
- dirhodium(II)
- lactams
- scCO(2)
- ASYMMETRIC CYCLOPROPANATION
- ALPHA-DIAZOACETAMIDES
- HOMOGENEOUS CATALYSIS
- SUPERCRITICAL FLUIDS
- CARBOXYLATES
- ENANTIOSELECTIVITY
- TRANSFORMATIONS
- IMMOBILIZATION
- ACTIVATION
- STRATEGY