New phosphine-diamine and phosphine-amino-alcohol tridentate ligands for ruthenium catalysed enantioselective hydrogenation of ketones and a concise lactone synthesis enabled by asymmetric reduction of cyano-ketones

Chemistry Central Journal

Volumn 6, Issue 1, 2012, Pages

  Fuentes, José A ^a   Phillips, Scott D ^a   Clarke, Matthew L ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Acrylonitrile; Asymmetric synthesis; Chiral alcohols; Homogeneous catalysis; Hydrogenation; Keto nitriles; Michael addition; Organocatalysis; P,N,N ligands; P,N,O ligands

Indexed keywords

EID: 84872177314     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/1752-153X-6-151     Document Type: Article

References (30)

1. De Vries JG, Elsevier CJ. Handbook of homogeneous hydrogenation 2007, Wiley VCH: Weinheim.
2. Noyori R, Ohkuma T. Asymmetric catalysis by architectural and functional molecular engineering: practical chemo- and stereoselective hydrogenation of ketones. Angew Chem Int Ed 2001, 40:40-73.
3. Ohkuma T, Ooka H, Hashiguchi S, Ikariya T, Noyori R. Practical enantioselective hydrogenation of aromatic ketones. J Am Chem Soc 1995, 117:2675-2676.
4. Ohkuma T, Sandoval CA, Srinivasan R, Lin Q, Wei Y, Muniz K, Noyori R. Asymmetric hydrogenation of tert-alkyl ketones. J Am Chem Soc 2005, 127:8288-8289.
5. Burk MJ, Hems W, Herzberg D, Malan C, Zanotti-Gerosa A. A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and alpha, beta-unsaturated ketones. Org Lett 2000, 2:4173-4176.
6. Clarke ML, Diaz-Valenzuela MB, Slawin AMZ. Hydrogenation of aldehydes, esters, imines, and ketones catalyzed by a ruthenium complex of a chiral tridentate ligand. Organometallics 2007, 26:16-19.
7. Abdur-Rashid K, Guo RW, Lough AJ, Morris RH, Song DT. Synthesis of ruthenium hydride complexes containing beta-aminophosphine ligands derived from amino acids and their use in the H2-hydrogenation of ketones and imines. Adv Synth Catal 2005, 347:571-579.
8. Baratta W, Ballico M, Chelucci G, Siega K, Rigo P. Osmium(II) CNN pincer complexes as efficient catalysts for both asymmetric transfer and H(2) hydrogenation of ketones. Angew Chem Int Ed 2008, 47:4362-4365.
9. Carpenter I, Eckelmann SC, Kuntz MT, Fuentes JA, France MB, Clarke ML. Convenient and improved protocols for the hydrogenation of esters using Ru catalysts derived from (P,P), (P,N,N) and (P,N,O) ligands. Dalton Trans 2012, 41:10136-10140.
10. Diaz-Valenzuela MB, Phillips SD, France MB, Gunn ME, Clarke ML. Enantioselective hydrogenation and transfer hydrogenation of bulky ketones catalysed by a ruthenium complex of a chiral tridentate ligand. Chem-Eur J 2009, 15:1227-1232.
11. Phillips SD, Andersson KHO, Kann N, Kuntz MT, France MB, Wawrzyniak P, Clarke ML. Exploring the role of phosphorus substituents on the enantioselectivity of Ru-catalysed ketone hydrogenation using tridentate phosphine-diamine ligands. Catal Sci Technol 2011, 1:1336-1339.
12. Phillips SD, Fuentes JA, Clarke ML. On the NH effect in ruthenium-catalysed hydrogenation of ketones: Rational design of phosphine-amino-alcohol ligands for asymmetric hydrogenation of ketones. Chem-Eur J 2010, 16:8002-8005.
13. Ito J, Ujiie S, Nishiyama H. New bis(oxazolinyl)phenyl-ruthenium(II) complexes and their catalytic activity for enantioselective hydrogenation and transfer hydrogenation of ketones. Organometallics 2009, 28:630-638.
14. Ito M, Endo Y, Ikariya T. Well-defined triflylamide-tethered arene-ru(tsdpen) complexes for catalytic asymmetric hydrogenation of ketones. Organometallics 2008, 27:6053-6055.
15. Jolley KE, Zanotti-Gerosa A, Hancock F, Dyke A, Grainger DM, Medlock JA, Nedden HG, Le Paih JJM, Roseblade SJ, Seger A, Sivakumar V, Prokes I, Morris DJ, Wills M. Application of tethered ruthenium catalysts to asymmetric hydrogenation of ketones, and the selective hydrogenation of aldehydes. Adv Synth Catal 2012, 354:2545-2555.
16. Naud F, Malan C, Spindler F, Ruggeberg C, Schmidt AT, Blaser HU. Ru-(phosphine-oxazoline) complexes as effective, industrially viable catalysts for the enantioselective hydrogenation of aryl ketones. Adv Synth Catal 2006, 348:47-50.
17. WWN O, Lough AJ, Morris RH. The hydrogenation of molecules with polar bonds catalyzed by a ruthenium(II) complex bearing a chelating N-heterocyclic carbene with a primary amine donor. Chem Commun 2010, 46:8240-8242.
18. Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T. Oxo-tethered ruthenium(II) complex as a bifunctional catalyst for asymmetric transfer hydrogenation and (H2) hydrogenation. J Am Chem Soc 2011, 133:14960-14963.
19. Ohkuma T, Utsumi N, Tsutsumi K, Murata K, Sandoval C, Noyori R. The hydrogenation/transfer hydrogenation network: asymmetric hydrogenation of ketones with chiral η6-arene/N-tosylethylenediamine - ruthenium(II) catalysts. J Am Chem Soc 2006, 128:8724-8725.
20. Wang C, Villa-Marcos B, Xiao JL. Hydrogenation of imino bonds with half-sandwich metal catalysts. Chem Commun 2011, 47:9773-9785.
21. Xu YJ, Alcock NW, Clarkson GJ, Docherty G, Woodward G, Wills M. Asymmetric hydrogenation of ketones using a ruthenium(II) catalyst containing binol-derived monodonor phosphorus-donor ligands. Org Lett 2004, 6:4105-4107.
22. Vigneron JP, Dhaehens M, Horeau A. Nouvelle methode pur porter au maximum la purete optique d'un produit partiellement dedouble sans l'aide d'aucune substance chirale. Tetrahedron 1973, 29:1055-1059.
23. Clarke ML, Roff GJ. Highly regioselective rhodium catalysed hydroformylation of unsaturated esters: the first practical method for quaternary selective carbonylation. Chem-Eur J 2006, 12:7978-7986.
24. Noonan GM, Cobley CJ, Lebl T, Clarke ML. Asymmetric hydroformylation of an enantiomerically pure bicyclic lactam; efficient synthesis of functionalised cyclopentylamines. Chem-Eur J 2010, 16:12788-12791.
25. Sabitha G, Bhaskar V, Yadav JS. The first asymmetric total synthesis of (R)-tuberolactone, (S)-jasmine lactone and (R)-delta-decalactone. Tetrahedron Lett 2006, 47:8179-8181.
26. Downham R, Edwards PJ, Entwistle DA, Hughes AB, Kim KS, Ley SV. Dispiroketals in synthesis 19. Dispiroketals as enantioselective and regioselective protective agents for symmetrical cyclic and acyclic polyols. Tetrahedron-Asymm 1995, 6:2403-2440.
27. Krimm H. Process for the production of α-monocyanoethyl ketones. US patent (Farbenfabrika Bayer Aktengesellshaft) US1958:2850519.
28. Wessig P, Muehling O. Photochemical synthesis of highly functionalised cyclopropyl ketones. Helv chim Acta 2003, 86:865-885.
29. Soltani O, Ariger MA, Henar VV, Carreira EM. Transfer Hydrogenation in water: enantioselective, catalytic reduction of alpha cyano and alpha nitro acetophenones. Org Lett 2010, 12:2893-2895.
30. Enthaler S, Junge K, Addis D, Erre G, Beller M. A practical and benign synthesis of primary amine through ruthenium-catalysed reduction of nitriles. Chemsus Chem 2008, 1:1006-1010.