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Synthesis and application of modular phosphine-phosphoramidite ligands in asymmetric hydroformylation: structure-selectivity relationship.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2010 Jan 18; Vol. 16 (3), pp. 871-7. - Publication Year :
- 2010
-
Abstract
- A series of hybrid phosphine-phosphoramidite ligands has been designed and synthesized in moderate yields from chiral BINOL (1,1'-bi-2-naphthol) or NOBIN (2-amino-2'-hydroxy-1,1'-binaphthyl). They have achieved highly regio- and enantioselectivities in Rh-catalyzed asymmetric hydroformylations of styrene derivatives (branched/linear ratio up to 56.6, ee up to 99 %), vinyl acetate derivatives (up to 98 % ee), and allyl cyanide (up to 96 % ee). Systematic variation of ligand structure showed that the steric factor on the phsophoramidite moiety determined the performance of the ligand. With the increased hindrance, the branched/linear ratio rose, while the ee value dropped in the hydroformylation of styrene. However, the N-substituents did not influence the selectivities much.
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 16
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 19950337
- Full Text :
- https://doi.org/10.1002/chem.200902238