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RuCl3/PPh3: an efficient combination for the preparation of chiral 1,3-anti-diols through catalytic hydrogenation
- Source :
- Organic Letters, Organic Letters, American Chemical Society, 2007, pp.105-108, Organic Letters, 2007, 9, pp.105-108
- Publication Year :
- 2006
-
Abstract
- [reaction: see text] An efficient economical alternative to the commonly used Evans' reagent for the diastereoselective reduction of beta-hydroxy ketones is reported. Thus, ruthenium-mediated hydrogenation of enantioenriched beta-hydroxy ketones using RuCl3 associated to achiral monophosphines allowed the preparation of a series of 1,3-anti-diols in good yields and with a high level of diastereoselectivity. A short screening of ligands pointed out PPh3 as the most effective phosphine, and PCy3 afforded the 1,3-diols with an unexpected moderate syn selectivity.
- Subjects :
- Noyori asymmetric hydrogenation
010402 general chemistry
Biochemistry
01 natural sciences
Catalysis
chemistry.chemical_compound
Organophosphorus Compounds
Organic chemistry
Physical and Theoretical Chemistry
ComputingMilieux_MISCELLANEOUS
Catalytic hydrogenation
Molecular Structure
[CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry
Organic Chemistry
Water
Stereoisomerism
General Medicine
Combinatorial chemistry
3. Good health
0104 chemical sciences
chemistry
Reagent
Ruthenium Compounds
Selectivity
Phosphine
Subjects
Details
- ISSN :
- 15237060 and 15237052
- Volume :
- 9
- Issue :
- 1
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....cba23daff0b61117f9e863e012d62bf4