Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Rhodium Block Copolymer Complexes in Aqueous Micelles

Shlomi Elias; Kerem Goren; Arkadi Vigalok

doi:10.1055/s-0032-1317487

Synlett, Table of Contents

Synlett 2012; 23(18): 2619-2622
DOI: 10.1055/s-0032-1317487

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Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Rhodium Block Copolymer Complexes in Aqueous Micelles

Shlomi Elias

School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel Fax: +972(3)6406205 Email: avigal@post.tau.ac.il

,

Kerem Goren

School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel Fax: +972(3)6406205 Email: avigal@post.tau.ac.il

,

Arkadi Vigalok*

School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel Fax: +972(3)6406205 Email: avigal@post.tau.ac.il

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Abstract

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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 - rhodium

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References

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

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