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Synlett 2012; 23(18): 2619-2622
DOI: 10.1055/s-0032-1317487
DOI: 10.1055/s-0032-1317487
letter
Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Rhodium Block Copolymer Complexes in Aqueous Micelles
Further Information
Publication History
Received: 09 August 2012
Accepted after revision: 25 September 2012
Publication Date:
18 October 2012 (online)
Abstract
High activity and enantioselectivity were achieved in the rhodium-catalyzed asymmetric transfer-hydrogenation reactions of ketones in pure water using a novel amphiphilic block polypeptide ligand. The covalent linkage of the catalyst to the block copolymer plays a significant role and provides higher conversions and better recyclability than regular micellar or nonmicellar systems.
Key words
asymmetric transfer hydrogenation - micellar catalysis - block copolymers - ketones - rhodiumSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
- 1 Sun Y, Liu G, Gu H, Huang T, Zhang Y, Li H. Chem. Commun. 2011; 47: 2583
- 2a Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
- 2b Sinou D. Adv. Synth. Catal. 2002; 344: 221
- 2c Eckl RW, Priermeier T, Herrmann WA. J. Organomet. Chem. 1997; 532: 243
- 3 Wu X, Vinci D, Ikariya T, Xiao J. Chem. Commun. 2005; 4447
- 4a Ikariya T, Murata K, Noyori R. Org. Biomol. Chem. 2006; 4: 393
- 4b Gladiali S, Albericob E. Chem. Soc. Rev. 2006; 35: 226
- 4c Morris RH. Chem. Soc. Rev. 2009; 38: 2282
- 4d Samec JS. M, Bäckvall JE, Andersson PG, Brandt P. Chem. Soc. Rev. 2006; 35: 237
- 4e Wu X, Wang C, Xiao J. Platinum Metals Rev. 2010; 54: 3
- 4f Dimroth J, Keilitz J, Schedler U, Schomäcker R, Haag R. Adv. Synth. Catal. 2010; 352: 2497
- 5a Li X, Chen W, Hems W, King F, Xiao J. Tetrahedron Lett. 2004; 45: 951
- 5b Li X, Wu X, Chen W, Hancock FE, King F, Xiao J. Org. Lett. 2004; 6: 3321
- 6a Kotre T, Zarka MT, Krause JO, Buchmeiser MR, Weberskirch R, Nuyken O. Macromol. Symp. 2004; 217: 203
- 6b Persigehl P, Jordan R, Nuyken O. Macromolecules 2000; 33: 6977
- 6c Schonfelder D, Fischer K, Schmidt M, Nuyken O, Weberskirch R. Macromolecules 2005; 38: 254
- 6d Zarka MT, Nuyken O, Weberskirch R. Macromol. Rapid Commun. 2004; 25: 858
- 7 Elias S, Vigalok A. Adv. Synth. Catal. 2009; 351: 1499
- 8 Kricheldorf HR. Angew. Chem. Int. Ed. 2006; 45: 5752
- 9 Cortez NA, Aguirre G, Parra-Hake M, Somanathan R. Tetrahedron Lett. 2009; 50: 2228
- 10 See, for example: Kim MS, Hyun H, Cho YH, Seo KS, Jang WY, Kim SK, Khang G, Lee HB. Polym. Bull. 2005; 55: 149
- 11 Shorter reaction times led to incomplete conversion indicating negligible catalyst leaching or decomposition during the recycling.
- 12 Ma Y, Liu H, Chen L, Cui X, Zhu J, Deng J. Org. Lett. 2003; 5: 2103
- 13 Trivedi R, Kompella UB. Nanomedicine (London) 2010; 5: 485
- 14 Terashima T, Ouchi M, Ando T, Sawamoto M. Polym. J. 2011; 43: 770