α-Amino-oximes based on optically pure limonene: A new ligands family for ruthenium-catalyzed asymmetric transfer hydrogenation

Chirality

Volumn 24, Issue 8, 2012, Pages 675-682

  Ibn El Alami, Mohammed Samir ^a,b,c   El Amrani, Mohamed Amin ^a   Dahdouh, Abdelaziz ^a   Roussel, Pascal ^b,c   Suisse, Isabelle ^b,c   Mortreux, André ^b,c  

^a FACULTÉ DES SCIENCES   (Morocco)

^b UNIV LILLE   (France)

^c UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

amino oxime; asymmetric transfer hydrogenation; limonene; ruthenium

Indexed keywords

ALPHA AMINO OXIME; HYDROGEN; KETONE; LIGAND; LIMONENE; OXIME DERIVATIVE; RUTHENIUM; RUTHENIUM AMINO OXIME COMPLEX; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; OPTICS; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 84864418770     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22073     Document Type: Article

References (47)

1. Noyori R, Hashiguchi S,. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc Chem Res 1997; 30: 97-102. (Pubitemid 127472554)
2. Palmer MJ, Wills M,. Asymmetric transfer hydrogenation of C=O and C=N bonds. Tetrahedron: Asymmetry 1999; 10: 2045-2061. (Pubitemid 29386760)
3. Wang C, Wu X, Xiao J,. Broader, greener, and more efficient: recent advances in asymmetric transfer hydrogenation. Chem Asian J 2008; 3: 1750-1770.
4. Ojima I, Catalytic asymmetric synthesis, 3th ed. New-York: Wiley-VCH, 2010.
5. Jacobsen EN, Pfaltz A, Yamamoto H,. Comprehensive asymmetric catalysis. Berlin: Springer, 1999.
6. Blaser HU, Federsel HJ,. Asymmetric catalysis on industrial scale. Weinheim: Wiley-VCH, 2010.
7. Blaser HU,. The chiral pool as a source of enantioselective catalysts and auxiliaries. Chem Rev 1992; 92: 935-952.
8. Nugent WA, RajanBabu TV, Burk MJ,. Beyond nature's chiral pool: enantioselective catalysis in industry. Science 1993; 259: 479-483.
9. Kagan HB, Dang TP,. Asymmetric catalytic reduction with transition metal complexes. Catalytic system of rhodium(I) with (-)-2,3-O-isopropylidene-2,3- dihydroxy-1,4-bis(diphenylphosphino)-butane, a new chiral phosphine. J Am Chem Soc 1972; 94: 6429-6433.
10. Khiar N, Navas R, Álvarez E, Fernández I,. New sulfur-phosphine ligands derived from sugars: synthesis and application in palladium-catalyzed allylic alkylation and in rhodium asymmetric hydrogenation. Arkivoc 2008; viii: 211-224.
11. Liu D, Li W, Zhang X,. A novel chiral ferrocenyl phosphine ligand from sugar: applications in Rh-catalyzed asymmetric hydrogenation reactions. Org Lett 2002; 4: 4471-4474.
12. Diéguez M, Ruiz A, Claver CJ,. Chiral diphosphites derived from D-glucose: new highly modular ligands for the asymmetric catalytic hydrogenation. Org Chem 2002; 67: 3796-3801. (Pubitemid 34563993)
13. Saitoh A, Uda T, Morimoto T,. A new class of C2-symmetric diphosphine ligands derived from valine: remarkably diverse behavior in catalytic asymmetric transformations. Tetrahedron Asymmetry 1999; 10: 4501-4511. (Pubitemid 30084674)
14. Agbossou-Niedercorn F, Suisse I,. Chiral aminophosphine phosphinite ligands and related auxiliaries: recent advances in their design, coordination chemistry, and use in enantioselective catalysis. Coord Chem Rev 2003; 242: 145-158.
15. Cimarelli C, Fratoni D, Palmieri G,. A convenient synthesis of new diamine, amino alcohol and aminophosphines chiral auxiliaries based on limonene oxide. Tetrahedron Asymmetry 2009; 20: 2234-2239.
16. Chrisman W, Camara JN, Marcellini K, Singaram B, Goralski CT, Hasha DL, Rudolf PR, Nicholson LW, Borodychuk KK,. A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide. Tetrahedron Lett 2001; 42: 5805-5807. (Pubitemid 32781617)
17. Robertson A, Bradaric C, Frampton CS, McNulty J, Capretta A,. Novel chiral phosphines derived from limonene: the synthesis and structure of 4,8-dimethyl-2-phosphabicyclo[3.3.1]nonane. Tetrahedron Lett 2001; 42: 2609-2612. (Pubitemid 32245511)
18. For some recent examples:, Hobuss D, Baro A, Laschat S, Frey W,. Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols. Tetrahedron 2008; 64: 1635-1640.
19. Malkov AV, Stewart-Liddon AJP, Teply F, Kobr L, Muir KW, Haigh D, Kocovsky P,. New pinene-derived pyridines as bidentate chiral ligands. Tetrahedron 2008; 64: 4011-4025.
20. Verendel JJ, Andersson PG,. Development of pinene-derived N,P ligands and their utility in catalytic asymmetric hydrogenation. Dalton Trans 2007; 47: 5603-5610. (Pubitemid 350176111)
21. Dvornikova IA, Frolova LL, Churakov AV, Kuchin AV,. New unsymmetrical salen-type ligand from enantiomerically pure 2-hydroxypinan-3-one. Russ Chem Bull Int Ed 2004; 53: 1323-1326. (Pubitemid 39273691)
22. Watts CC, Thoniyot P, Hirayama LC, Romano T, Singaram B,. Enantioselective alkynylations of aromatic and aliphatic aldehydes catalyzed by terpene derived chiral amino alcohols. Tetrahedron Asymmetry 2005; 16: 1829-1835. (Pubitemid 40719808)
23. Suzuki T, Shibata A, Morohashi N, Ohba Y,. Synthesis and characterization of novel chiral 1,2-diamines derived from α-pinene. Chem Lett 2005; 34: 1476-1477. (Pubitemid 43162182)
24. Krzeminski MP, Wojtczak A,. Chiral terpene auxiliaries. Part 1: highly enantioselective reduction of ketones with borane catalyzed by an oxazaborolidine derived from (-)-β-pinene. Tetrahedron Lett 2005; 46: 8299-8302. (Pubitemid 41560852)
25. Szakonyi Z, Balazs A, Martinek TA, Fülöp F,. Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (-)-α-pinene. Tetrahedron Asymmetry 2006; 17: 199-204. (Pubitemid 43226628)
26. Gavryushin A, Polborn K, Knochel P,. Novel chiral diphosphine ligands with a pinene core obtained via an allylphosphinite-allylphosphine oxide rearrangement. Tetrahedron Asymmetry 2004; 15: 2279-2288. (Pubitemid 39036861)
27. Malkov AV, Bella M, Stara IG, Kocovsky P,. Modular pyridine-type P,N-ligands derived from monoterpenes: application in asymmetric Heck addition. Tetrahedron Lett 2001; 42: 3045-3048. (Pubitemid 32276041)
28. ElAlami S, Dahbouh AA, Ibn Mansour A, ElAmrani MA, Suisse I, Agbossou-Niedercorn F, Mortreux A,. Synthesis of chiral bifunctional ligands based on α-pinene and their use in ruthenium catalyzed asymmetric transfer hydrogenation. CR Chimie 2009; 12: 1253-1258.
29. Kirin VP, Prikhod'ko IY, Maksakov VA, Virovets AV, Agafontsev AM, Golovin BA,. Ruthenium carbonyl complexes with α-substituted oxime derivatives of terpenes as ligands. Russ Chem Bull Int Ed 2009; 58: 1371-1382.
30. Tkachev AV, Rukavishnikov AV, Chibiryaev AM, Denisov AY, Gatilov YV, Bagryanskaya IY,. Stereochemistry of α-amino oximes from the terpene hydrocarbons car-3-ene, limonene and α-pinene. Aust J Chem 1992; 45: 1077-1086.
31. Petukhov PA, Bizyaev SN, Tkachev AV,. Synthesis of α-amino oximes and bis- α-amino oximes from the monoterpene hydrocarbons 3-carene and α-pinene and α,Ï-diamines. Russ Chem Bull Int Ed 2001; 50: 2106-2112. (Pubitemid 33392030)
32. Carman R, Mathew PC, Saraswathi GN, Singaram B, Verghese J,. Amino oximes from p-menth-1-ene, limonene and α-pinene. Aust J Chem 1977; 30: 1323-1335.
33. Pastor IM, Västilä P, Adolfsson H,. Employing the structural diversity of nature: development of modular dipeptide-analogue ligands for ruthenium-catalyzed enantioselective transfer hydrogenation of ketones. Chem Eur J 2003; 9: 4031-4045.
34. Comasseto JV, Andrade LH, Omori AT, Assis LF, Meleiro Porto AL,. Deracemization of aryl ethanols and reduction of acetophenones by whole fungal cells of Aspergillus terreus CCT 4083, A. terreus CCT 3320 and Rhizopus oryzae CCT. J Mol Catal B 2004; 29: 55-61. (Pubitemid 38624073)
35. Zhang XC, Wu Y, Yu F, Wu FF, Wu J, Chan ASC,. Chem Eur J 2009; 15: 5888-5891.
36. Yu F, Zhang XC, Wu FF, Zhou JN, Fang W, Wu J, Chan ASC,. Org Biomol Chem 2011; 16: 5652-5654.
37. Palatinus L, Chapuis G,. SUPERFLIP-a computer program for the solution of crystal structures by charge flipping in arbitrary dimensions. J Appl Cryst 2007; 40: 786-790. (Pubitemid 47080274)
38. Betteridge PW, Carruthers JR, Cooper RI, Prout K, Watkin DJ,. CRYSTALS version 12: software for guided crystal structure analysis. J Appl Cryst 2003; 36: 1487.
39. Spek AL,. PLATON, a multipurpose crystallographic tool, Utrecht University, Utrecht, The Netherlands, 2002.
40. Petra DGI, Kamer PCJ, van Leeuwen PWNM, Goubitz K, Van Loon AM, de Vries JG, Schoemaker HE,. Amino alcohol coordination in ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones. Eur J Inorg Chem 1999; 1999: 2335-2341.
41. Everaere K, Mortreux A, Bulliard M, Brussee J, van de Gen A, Nowogrocki G, Carpentier JF,. (β-amino alcohol)(arene)ruthenium(II)-catalyzed asymmetric transfer hydrogenation-Scope, isolation of the catalytic intermediates, and deactivation processes. Eur J Org Chem 2001; 2001: 275-291. (Pubitemid 32104361)
42. Hashigushi S, Fujii A, Takehara J, Takehara I, Ikariya T, Noyori R,. Asymmetric transfer hydrogenation of aromatic ketones catalyzed by chiral ruthenium(II) complexes. J Am Chem Soc 1995; 117: 7562-7563.
43. Gladiali S, Alberico E,. Asymmetric transfer hydrogenation: chiral ligands and applications. Chem Soc Rev 2006; 35: 226-236. (Pubitemid 43327144)
44. Hashiguchi S, Noyori R,. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc Chem Res 1997; 30: 97-102. (Pubitemid 127472554)
45. II-promoted asymmetric hydrogen transfer between alcohols and ketones. Angew Chem Int Ed Engl 1997; 36: 285-288.
46. Singh SK, Sharma S, Dwivedi SD, Zou RQ, Xu Q, Pandey DS,. Reactivity of the oxime/oximato group in ruthenium (II) complexes. Inorg Chem 2008; 47: 11942-11949.
47. Pannetier N, Sortais JB, Dieng PS, Barloy L, Sirlin C, Pfeffer M,. Kinetics and mechanism of ruthenacycle-catalyzed asymmetric hydrogen transfer. Organometallics 2008; 27: 5852-5859.