Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 3, Pages 871-877Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902238
Keywords
asymmetric catalysis; enantioselectivity; hydroformylation; phosphine-phosphoramidite ligands; rhodium
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Funding
- National Institutes of Health [GM58832]
- Merck Co., Inc.
- National Center for Research Resources (NCRR) [1S10RR023698-01A1]
- NATIONAL CENTER FOR RESEARCH RESOURCES [S10RR023698] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM058832] Funding Source: NIH RePORTER
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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.
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