I want to do chiral reduction of an asymmetrical ketone RCOR1 to corrosponding chiral alcohol R or S by hydrogenation. Is it possible? Kindly provide me some information if some one has carried out similar reactions using some catalysts.
You might check out the work of Dr Rhett Kempe (Inorganic Chemistry II, University Bayreuth), he prepared nice Iridium catalysts for the enantioselective hydrogenation of asymmetrical ketones giving quite enantiopure alcohols (ee >99%). As far as I know these catalysts are pretty cheap compared with the common commercially available catalysts. He's got a small company which sells these Iridium catalysts if you don't want to prepare them yourself.
I am agree with Bernhard suggestion. Prof. kempe group synthesised some new amido-iridium catalyst for the hydrogenation of simple ketones in Angwante chemie 2011.
Your question and substrate are broad enough to require a maybe. The transformation is substrate and catalyst specific. Combi ie trial and error of a range of reagents provides a solution. It can be done but no magic bullet.
Commercially resolution chemical and enzyme work with Mutsuhito of distomer.
Just look for Noyori's work on ketone hydrogenation by either transfer or true hydrogenation. Other work of intest in this context is by Walter Baratta, Rhett Kempe, or also Robert Morris of Toronto.
On of their systems should work. Companies to ask for could be Solvias or Johnson Mattay or (at least in the past) Dr. Reddy's. Good luck
Chiral ruthenium complexes are known as excellent catalysts for
asymmetric transfer hydrogenation, as Nosrat O Mahmood suggests, above. I've carried out very efficient ruthenium catalyzed hydrogenations but not specifically for chiral. products.
Take a look at: http://pubs.acs.org/doi/abs/10.1021/ja0620989
Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, Issue 18, 2011
1,4-Diazabicyclo[2.2.2]octane as an Efficient Catalyst for a Clean, One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives via Multicomponent Reaction in Aqueous Media
You can see the literarute regarding this. Check for the appropriate chiral organocatalyst for the same. Also please refer to the Prof. Sudalai's research papers from NCL Pune. He has some papers in this regard.
Al-complex such vitride in selective mole if we use then we can reduce complete or partial for the ketone functional group & Biological enzymes also reduce the carbonyl group selectively.
William Berkowitz sent you a message on ResearchGate. (This may be a repeat).
Hi,
Asymmetric reduction of an amide of alpha-amino-acetophenones, see any one of the following, then hydrolyse the hydroxy-amide product back to the amino alcohol.
With borane-THF, borrole, (R)-tetrahydro-1-Me-3,3-Ph2-1H,3H-pyrrolo[1,2-c][1,3-2]oxaza in toluene, T= 5 - 20 °C
Coe, Diane M.; Perciaccante, Rossana; Procopiou, Panayiotis A.; Organic and Biomolecular Chemistry; vol. 1; nb.
7; (2003); p. 1106 – 1111
in ethanol, water, Time= 504h, T= 32 °C , baker's yeast, sucrose, Yield given. Yields of byproduct given. Title compound
not separated from byproducts
Izumi, Taeko; Fukaya, Katsumi; Bulletin of the Chemical Society of Japan; vol. 66; nb. 4; (1993); p. 1216 - 1221
With palladium (II) trifluoroacetate, hydrogen, (R,R)-Me-duphos in 2,2,2-trifluoroethanol, p= 10343 - 20685.9Torr ,
Heating, Title compound not separated from byproducts
You can reduce using asymmetric transfer hydrogenation by RuCl2-p-cymene combined with chiral aminoalcohols or chiral diamines in isopropanol in the presence of NaOH under nitrogen.
You might want to try DIPCl, HC Brown's reagent. We got very high ee's when using DIPCl to reduce pro-chiral alpha amino ketones to the corresponding amino alcohols. DIPCl has the added advantage of being available in both enantiomers of alpha-pinene, so obtaining R or S enantiomers after the reduction is quite direct.