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Generation of chiral phosphonium dialkyl phosphite as a highly reactive p-nucleophile: application to asymmetric hydrophosphonylation of aldehydes
- Source :
- Journal of the American Chemical Society. March 25, 2009, Vol. 131 Issue 11, 3836-3837
- Publication Year :
- 2009
-
Abstract
- The generation of chiral tetraaminophosphonium dialkyl phosphite is detected by low-temperature NMR analysis and its synthetic potential as a reactive P-nucleophile is shown by its application to the establishment of highly efficient and enantioselective hydrophosphonylation of various aldehydes. The analysis of the organic-base-dependent generation of the ion pair and its reactivity and selectivity as a P-nucleophile has shown that the structure of the cationic conjugate acid of the base is a major factor for generation of phosphite anions with nucleophilicity and rigorous stereocontrol.
Details
- Language :
- English
- ISSN :
- 00027863
- Volume :
- 131
- Issue :
- 11
- Database :
- Gale General OneFile
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.200351694