Asymmetric hydrogenation Noyori

Noyori, R. In Asymmetric Catalysis in Organic Synthesis Ojima, I., ed. Wiley New York, 1994, chapter 2. 

Asymmetric reduction of carbonyl via hydrogenation catalyzed by ruthenium(II) BINAP complex. 

Noyori, R. Ohta, M. Hsiao, Y. Kitamura, Ma. Ohta, T. Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Ryoji Noyori (Japan, 1938—) and Herbert William S. Knowles (USA, 1917—) shared half of the Nobel Prize in Chemistry in 2001 for their work on chirally catalyzed hydrogenation reactions. K. Barry Sharpless (USA, 1941—) shared the other half for his work on chirally catalyzed oxidation reactions. 

Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008. (Review, Nobel Prize Address). 

Cr-Ni bimetallic catalyst-promoted redox addition of vinyl halides to aldehydes. 

Asymmetric reduction of carbonyls and alkenes via hydrogenation, catalyzed by a mthenium(ll) BINAP complex. 

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 182, Springer-Verlag Berlin Heidelberg 2009 

Noyori asymmetric hydrogenation. In Name Reactions for Functional Group Transformations, Li, J. J., Corey, E. J., Eds. John Wiley Sons Hoboken, NJ, 2007, pp 46-66. (Review). 

Asymmetric reduction of carboryls and aikenes via hydrogenation, catalyzed by a rathenium(TI) BINAP conqilex. 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 195, Springer International Publishing Switzerland 2014 

aryl R = alkyl, aryl Z = nitrogen, oxygen, halogen Y = sp or sp hybridized carbon n =1-3 X = halogen  

The total synthesis of pentacyclic alkaloid (-)-haliclonadiamine was accomplished by D.F. Taber and co-workers. The Noyori asymmetric hydrogenation was used to prepare a bicyclic 3-hydroxy ester intermediate in enantiopure form from a racemic bicyclic P-keto ester via kinetic resolution. It was found that the hydrogenation only took place in the presence of added HCI and by optimizing the amount of HCI added, the proportion of the total reduced ketone could be controlled. About 87% of the matched ketone was reduced, while the other P-keto ester enantiomer was not significantly converted to the reduced product. Interestingly, the diastereoselectivity of the hydrogenation depended on the nature of the added acid with HCI, the trans diastereomer was the major product, while with AcOH the cis diastereomer was dominant. 

A pronounced enhancement of stereoselectivity was observed in the asymmetric hydrogenation of 2-substituted 2- 

The Noyori asymmetric transfer hydrogenation was utilized in the synthesis of the chiral 1,2,3,4-tetrahydroisoquinolines by R.A. Sheldon et al. These compounds are important intermediates in the Rice and Beyerman routes to morphine. The Rice imine was exposed to a series of chiral Ru complexes, which was prepared from r -arene-Ru chloride dimeric complexes and A/-sulfonated 1,2-diphenylethylenediamines along with the azeotropic mixture of HCOOH/NEts. With the best catalyst the desired tetrahydroisoquinoline was isolated in 73% yield and the enantiomeric excess was 99%. 

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J.-L Xiao, S. C. A Nefkens, P. G. Jessop, T. Ikariya, R. Noyori, Asymmetric Hydrogenation of a, -Unsaturated Carboxylic Adds in Supercritical Carbon Dioxide , Tetrahedron Lett. 1996,37,2813-2816. 

E. Katayama, T. Yokozawa, T. Ikaeiya, and R. Noyori, Asymmetric hydrogenation of alkenyl, cyclopropyl, and aryl ketones. RuCl2(xylbinap)(l,2-diamine) as a precatalyst exhibiting a wide scope, J. Am. Chem. Soc. 1998, 120, 13529-13530. 

A diastereoselective Mukaiyama aldol lactonization between thiopyridylsilylketene acetals and aldehydes was used to form the /3-lactone ring in the total synthesis of (-)-panclicin D <1997T16471>. Noyori asymmetric hydrogenation was a key step in a total synthesis of panclicins A-E and was used to establish the stereocenter in aldehyde 140, which in turn directed the stereochemistry of subsequent reactions <1998J(P1)1373>. The /3-lactone ring was then formed by a [2+2] cycloaddition reaction of 140 with alkyl(trimethylsilyl)ketenes and a Lewis acid catalyst. 

T. Ohkuma, M. Kitamura, R. Noyori, Asymmetric Hydrogenation, in Catalytic Asymmetric Synthesis (I. Ojima, Ed.), Wiley-VCH, New York, 2nd ed., 2000, 1-110. 

Noyori asymmetric hydrogenation Formation of enantio-enriched carboxylic acids, alcohols and amino acids from unsaturated carboxylic acids, allylic alcohols and enamides, respectively. 316... 

Related reactions Corey-Bakshi-Shibata (CBS) reduction, Noyori asymmetric hydrogenation ... 

The asymmetry in 5-hydroxy-5,6-dihydropyran-2-ones, which form the basis of the phomopsolides, is derived from the Noyori asymmetric hydrogenation of a furyl ketone. The resulting furyl alcohol is then stereoselectively transformed into the pyranone <04TL1005>. 

This preliminary phase of the luzopeptin program had nonetheless validated our approach to 58, which we now wanted in nonracemic form. This required an enantioenriched variant of 56, which would be available from an appropriate P-ketoester either by a Noyori asymmetric hydrogenation or through baker s yeast reduction. We ultimately opted for a technically simpler yeast reduction on the basis of the excellent results reported with substrate 68, and we were not to be... 

The vinyl ether 219 was synthesized as shown in Scheme 49. Noyori asymmetric hydrogenation of a j6-keto ester derived from 224 generated the stereo-genic center in 225 with > 95% ee. According to Bunnelle s method [99], 225 was converted into allylsilane 226. Rychnovsky developed a new method for preparing vinyl ether, because of its sensitivity chloroacetylation and... 

Mechanistic insight into Noyori asymmetric hydrogenations of enamides, allylic alcohols, Q, )S-unsaturated carboxylic acids, o ,jS-keto esters, and aromatic ketones using Ru(OAc)2[(5)-binap], (3), as the catalyst has been highlighted ... 

J Xiao, SCA Nefkens, PG Jessop, T Ikariya, R Noyori. Asymmetric hydrogenation of a,fi-unsaturated carboxylic acids in supercritical carbon dioxide. Tetrahedron Lett 37 2813-2816, 1996. 

T Ohta, H Takaya, M Kitamura, K Nagai, R Noyori. Asymmetric hydrogenation of unsaturated carboxyhc acids catalyzed by BINAP-ruthenium(II) complexes. J Org Chem 52 3174-3176, 1987. 

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