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N-phosphino-p-tolylsulfinamide ligands: synthesis, stability, and application to the intermolecular Pauson-Khand reaction.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2008 Sep 19; Vol. 73 (18), pp. 7080-7. Date of Electronic Publication: 2008 Aug 26. - Publication Year :
- 2008
-
Abstract
- Here we synthesized a family of racemic and optically pure N-phosphino-p-tolylsulfinamide (PNSO) ligands. Their stability and coordination behavior toward dicobalt-alkyne complexes was evaluated. Selectivities of up to 3:1 were achieved in the ligand exchange process with (mu-TMSC2H)Co2(CO)6. The resulting optically pure major complexes were tested in the asymmetric intermolecular Pauson-Khand reaction and yielded up to 94% ee. X-ray studies of the major complex 18a indicated that the presence of an aryl group on the sulfinamide reduces the hemilabile character of the PNSO ligands.
- Subjects :
- Boranes chemistry
Crystallography, X-Ray
Ligands
Models, Molecular
Molecular Structure
Stereoisomerism
Cobalt chemistry
Organometallic Compounds chemical synthesis
Organometallic Compounds chemistry
Sulfonamides chemical synthesis
Sulfonamides chemistry
Toluene chemical synthesis
Toluene chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 73
- Issue :
- 18
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 18729408
- Full Text :
- https://doi.org/10.1021/jo800710n