Citation:
Gao-Feng Zha, Wei-Yun Xu, Peng Dai, Xiao-Yan Lai, Wei Liu, Yong-Cun Shen. A simple synthetic approach for the transformation of (S)-Ugi’s amine[J]. Chinese Chemical Letters,
;2014, 25(9): 1301-1304.
doi:
10.1016/j.cclet.2014.06.009
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A simple synthetic approach for the transformation of (S)-Ugi's amine, another configuration of (R)-Ugi's amine, one of the most widely used intermediate in the preparation of chiral ferrocene-based ligands, has been developed via esterification using anhydride, alkaline hydrolysis and active manganese dioxide oxidation, and the corresponding ferrocenyl ketone was afforded in good yields.
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Keywords:
- (S)-Ugi’s amine,
- Transformation,
- Esterification,
- Hydrolysis,
- Oxidation
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[1]
[1] (a) R.C.J. Atkinson, V.C. Gibson, N.J. Long, The syntheses and catalytic applications of unsymmetrical ferrocene ligands, Chem. Soc. Rev. 33 (2004) 313-328; (b) R.G. Arrayás, J. Adio, J.C. Carretero, Recent applications of chiral ferrocene ligands in asymmetric catalysis, Angew. Chem. Int. Ed. 45 (2006) 7674-7715; (c) J.C. Kizirian, Chiral tertiary diamines in asymmetric synthesis, Chem. Rev. 108 (2008) 140-205.
-
[2]
[2] N.W. Boaz, S.D. Debenham, E.B. Mackenzie, S.E. Large, Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis, Org. Lett. 4 (2002) 2421-2424.
-
[3]
[3] A. Togni, C. Breutel, A. Schnyder, et al., A novel easily accessible chiral ferrocenyldiphosphine for highly enantioselective hydrogenation, allylic alkylation, and hydroboration reactions, J. Am. Chem. Soc. 116 (1994) 4062-4066.
-
[4]
[4] (a) T. Ireland, G. Grossheimann, C. Wieser-Jeunesse, P. Knochel, Ferrocenyl ligands with two phosphanyl substituents in the α,ω positions for the transition metal catalyzed asymmetric hydrogenation of functionalized double bonds, Angew. Chem. Int. Ed. 38 (1999) 3212-3215; (b) T. Ireland, K. Tappe, G. Grossheimann, P. Knochel, Synthesis of a new class of chiral 1,5-diphosphanylferrocene ligands and their use in enantioselective hydrogenation, Chem. Eur. J. 8 (2002) 843-852.
-
[5]
[5] T. Sturm, W. Weissensteiner, F. Spindler, A novel class of ferrocenyl-aryl-based diphosphine ligands for Rh-and Ru-catalysed enantioselective hydrogenation, Adv. Synth. Catal. 345 (2003) 160-164.
-
[6]
[6] (a) T. Hayashi, T. Mise, M. Fukushima, et al., Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. I. Preparation of chiral ferrocenylphosphines, Bull. Chem. Soc. Jpn. 53 (1980) 1138-1151; (b) J.J.A. Perea, M. Lotz, P. Knochel, Synthesis and application of C2-symmetric diamino FERRIPHOS as ligands for enantioselective Rh-catalyzed preparation of chiral α-amino acids, Tetrahedron: Asymmetry 10 (1999) 375-384.
-
[7]
[7] (a) M. Lotz, T. Ireland, J.J.A. Perea, P. Knochel, Stereoselective substitution of α-aminoalkylferrocenes with diorganozincs. A fast synthesis of new chiral FERRIPHOS ligands for asymmetric catalysis, Tetrahedron: Asymmetry 10 (1999) 1839-1842; (b) J. Kang, J.H. Lee, J.B. Kim, G.J. Kim, Asymmetric modular synthesis of cylindrically chiral FerroPHOS ligands for the Rh-catalyzed asymmetric hydroboration, Chirality 12 (2000) 378-382.
-
[8]
[8] (a) P. Barbaro, A. Togni, A new chiral tridentate ferrocenyl ligand synthesis and characterization of its palladium (ii) and nickel (ii) complexes, Organometallics 14 (1995) 3570-3573; (b) L. Fadini, A. Togni, Ni (II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins, Chem. Commun. (2003) 30-31.
-
[9]
[9] R. Kuwano, K. Sato, T. Kurokawa, D. Karube, Y. Ito, Catalytic asymmetric hydrogenation of heteroaromatic compounds, indoles, J. Am. Chem. Soc. 122 (2000) 7614-7615.
-
[10]
[10] (a) D. Marquarding, H. Klusacek, G. Gokel, P. Hoffman, I. Ugi, Stereoselective syntheses. VI. Correlation of central and planar chirality in ferrocene derivatives, J. Am. Chem. Soc. 92 (1970) 5389-5393; (b) G.W. Gokel, D. Marquarding, I.K. Ugi, Stereoselective syntheses. VIII. Retentive nucleophilic displacements of alpha-substituted alkylferrocenes, J. Org. Chem. 37 (1972) 3052-3058.
-
[11]
[11] (a) H.C.L. Abbenhuis, U. Burchkhardt, V. GramLich, et al., A new stereoselective approach to chiral ferrocenyl ligands for asymmetric catalysis, Organometallics 13 (1994) 4481-4493; (b) H.C.L. Abbenhuis, U. Burchkhardt, V. GramLich, et al., Comparing chiral ferrocenyl and ruthenocenyl ligands: how subtle structural changes influence their performance in asymmetric catalysis, Organometallics 15 (1996) 1614-1621.
-
[12]
[12] T. Suzuka, M. Ogasawara, T. Hayashi, Asymmetric synthesis of metallocenes through enantioselective addition of organolithium reagents to 6-(dimethylamino) fulvene, J. Org. Chem. 67 (2002) 3355-3359.
-
[13]
[13] (a) W.S. Lam, S.H.L. Kok, T.T.L.A. Yeung, et al., An efficient approach to chiral ferrocene-based secondary alcohols via asymmetric hydrogenation of ferrocenyl ketones, Adv. Synth. Catal. 348 (2006) 370-374; (b) Y. Xu, S.L. Yu, Y.Y. Li, Z.R. Dong, J.X. Gao, Novel chiral C2-symmetric multidentate aminophosphine ligands for use in catalytic asymmetric reduction of ketones, Chin. Chem. Lett. 24 (2013) 527-530.
-
[14]
[14] (a) Y. Matsumoto, A. Ohno, S.J. Lu, T. Hayashi, Enantioselective synthesis of 1-metallocenylalkanols by catalytic asymmetric alkylation of metallocenecarboxaldehydes with dialkylzincs, Tetrahedron: Asymmetry 4 (1993) 1763-1766; (b) J. Wright, L. Frambes, P. Reeves, A simple route to chiral ferrocenyl alcohols, J. Organomet. Chem. 476 (1994) 215-217; (c) S. Hashiguchi, A. Fujii, K.L. Haack, et al., Kinetic resolution of racemic secondary alcohols by RuII-catalyzed hydrogen transfer, Angew. Chem. Int. Ed. 36 (1997) 288-290; (d) C. Bolm, K. Muñ iz, Catalytic enantioselective aryl transfer: asymmetric addition of diphenylzinc to aldehydes, Chem. Commun. (1999) 1295-1296; (e) Y. Nishibayashi, A. Yamauchi, G. Onodera, S. Uemura, Oxidative kinetic resolution of racemic alcohols catalyzed by chiral ferrocenyloxazolinylphosphine-ruthenium complexes, J. Org. Chem. 68 (2003) 5875-5880.
-
[15]
[15] W. Chen, W. Mbafor, S.M. Roberts, J. Whittall, A very simple, highly stereoselective and modular synthesis of ferrocene-based P-Chiral phosphine ligands, J. Am. Chem. Soc. 128 (2006) 3922-3923.
-
[16]
[16] G. Nicolosi, A. Patti, M. Piattelli, Lipase-mediated separation of the stereoisomers of 1-(1-hydroxyethyl)-2-(hydroxymethyl)ferrocene, J. Org. Chem. 59 (1994) 251-254.
-
[17]
[17] J. Attenburrow, A.F.B. Cameron, J.H. Chapman, et al., A synthesis of vitamin A from cyclohexanone, J. Chem. Soc. (1952) 1094-1111.
-
[18]
[18] P. Gogoi, G.K. Sarmah, D. Konwar, DMSO/N2H4 H2O/I2/H2O/CH3CN: a new system for selective oxidation of alcohols in hydrated media, J. Org. Chem. 69 (2004) 5153-5154.
-
[19]
[19] E.J. Corey, J.W. Suggs, Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds, Tetrahedron Lett. 16 (1975) 2647-2650.
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