Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts

Abstract

A highly efficient iridium-catalyzed asymmetric hydrogenation of α-amino ketones for the synthesis of chiral 1,2-amino alcohols is described. With chiral spiro iridium catalyst Ir-(R)-1c, a series of α-amino ketones were hydrogenated to chiral β-amino alcohols in excellent enantioselectivities (up to 99.9% ee) with TON up to 100 000. In addition, with this highly efficient method the chiral drugs (R)-clorpenaline and (R)-phenylephrine were prepared in very high efficiency.

Key words

asymmetric hydrogenation - chiral spiro catalysts - amino ketones - amino alcohols - iridium catalysts

• References

• 1a Ohkuma T, Noyori R In The Handbook of Homogeneous Hydrogenation . de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 1106
• 1b Noyori R, Okuma T. Angew. Chem. Int. Ed. 2001; 40: 40
• 1c Tang WJ, Zhang X. Chem. Rev. 2003; 103: 3029
• 1d Xie J.-H, Zhou Q.-L. Acta Chim. Sinica 2012; 70: 1427 ; Chem. Abstr. 2012, 157, 492267
• 1e Zhao B, Han Z, Ding K. Angew Chem. Int. Ed. 2013; 52: 4744

For reviews, see:
• 2a Ager DJ, Prakash I, Schaad DR. Chem. Rev. 1996; 96: 835
• 2b Bergmeier SC. Tetrahedron 2000; 56: 2561

For reviews, see:
• 3a Klingler FD. Acc. Chem. Res. 2007; 40: 1367
• 3b Mortreux A, Karim A In The Handbook of Homogeneous Hydrogenation . de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 1165-1192
• 3c Shang G, Li W, Zhang X In Catalytic Asymmetric Synthesis . 3rd ed.; Ojima I. Wiley; Hoboken: 2010: 343-436
• 4a Takeda H, Tachinami T, Aburatani M, Takahashi H, Morimoto T, Achiwa K. Tetrahedron Lett. 1989; 30: 367
• 4b McGarrity JF, Zanotti-Gerosa A. Tetrahedron: Asymmetry 2010; 21: 2479
• 5 The Merck Index . 14th ed. Merck and Co. Inc; Whitehouse Station: 2006
• 6 Shang G, Liu D, Allen SE, Yang Q, Zhang X. Chem. Eur. J. 2007; 13: 7780
• 7a Yokoyama H, Yanagisawa T, Taira N. J. Cardiovasc. Pharmacol. 1988; 12: 323
• 7b Bristow MR, Hershberger RE, Port JD, Minobe W, Rasmussen R. Mol. Pharmacol. 1989; 35: 295

See references 4a, 6 and:
• 8a Hayashi T, Katsumura A, Konishi M, Kumada M. Tetrahedron Lett. 1979; 20: 425
• 8b Kitamura M, Ohkuma T, Inoue S, Sayo N, Kumobayashi H, Akutagawa S, Ohta T, Takaya H, Noyori R. J. Am. Chem. Soc. 1988; 110: 629
• 8c Takeda H, Tachinami T, Aburatani M, Takahashi H, Morimoto T, Achiwa K. Tetrahedron Lett. 1989; 30: 363
• 8d Hayashi H, Sakuraba S, Takeda H, Achiwa K. J. Am. Chem. Soc. 1990; 112: 5876
• 8e Sakuraba S, Takahashi H, Takeda H, Achiwa K. Chem. Pharm. Bull. 1995; 43: 738
• 8f Devocelle M, Agbossou F, Mortreux A. Synlett 1997; 1306

See reference 4b and:
• 9a Mashima K, Kusano K.-H, Sato N, Matsumura Y.-i, Nozaki K, Kumobayashi H, Sayo N, Hori Y, Ishizaki T. J. Org. Chem. 1994; 59: 3064
• 9b Ohkuma T, Ishii D, Takeno H, Noyori R. J. Am. Chem. Soc. 2000; 122: 6510
• 9c Lei A, Wu S, He M, Zhang X. J. Am. Chem. Soc. 2004; 126: 1626
• 10 Wang Y.-Q, Lu S.-M, Zhou Y.-G. Org. Lett. 2005; 7: 3235
• 11 For example, see ref. 4b and 8c.
• 12a Xie J.-H, Liu X.-Y, Xie J.-B, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2011; 50: 7329
• 12b Xie J.-H, Liu X.-Y, Yang X.-H, Xie J.-B, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2012; 51: 201
• 12c Zhang Q.-Q, Xie J.-H, Yang X.-H, Xie J.-B, Zhou Q.-L. Org. Lett. 2012; 14: 6158
• 12d Yang X.-H, Xie J.-H, Liu W.-P, Zhou Q.-L. Angew. Chem. Int. Ed. 2013; 52: 7833
• 12e Yang X.-H, Xie J.-H, Zhou Q.-L. Org. Chem. Front. 2014; 1: 190
• 13a Liu S, Xie J.-H, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2007; 46: 7506
• 13b Liu S, Xie J.-H, Li W, Kong W.-L, Wang L.-X, Zhou Q.-L. Org. Lett. 2009; 11: 4994
• 13c Xie J.-H, Liu S, Kong W.-L, Bai W.-J, Wang X.-C, Wang L.-X, Zhou Q.-L. J. Am. Chem. Soc. 2009; 131: 4222
• 14 Graziani and co-workers reported that the iridium complex of chiral diphosphine ligand prolophos can catalyze the hydrogenation of α-amino ketones, but the enantioselectivi-ties were low (<31% ee); see: Cesarotti E, Parti L, Palliavicini M, Villa L, Spogliarich R, Farnetti E, Graziani M. J. Mol. Catal. 1990; 62: L29
• 15 Tatsumi K, Arima N, Yamato C, Yoshimura H, Tsukamoto H. Chem. Pharm. Bull. 1970; 18: 1254
• 16a Blaser H.-U, Spindler F, Thommen M In The Handbook of Homogeneous Hydrogenation . de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 1279
• 16b Gurjar MK, Krishna LM, Sarma B, Chorghade MS. Org. Process Res. Dev. 1998; 2: 422
• 16c Pandey RK, Upadhyay PK, Kumar P. Tetrahedron Lett. 2003; 44: 6245
• 17 Chong H.-S, Ma X, Lee H, Bui P, Song HA, Birch N. J. Med. Chem. 2008; 51: 2208
• 18 Miyano S, Lu LD, Viti SM, Sharpless KB. J. Org. Chem. 1983; 48: 3608
• 19 Corrigan JR, Sullivan M.-J, Bishop HW, Ruddy AW. J. Am. Chem. Soc. 1953; 75: 6258
• 20 Lutz RE, Allison RK, Ashburn G, Bailey PS, Clark MT, Codington JF, Deinet AJ, Freek JA, Jordan RH, Leake NH, Martin TA, Nicodemus KC, Rowlett RJ, Shearer NH, Smith JD, Wilson JW. J. Org. Chem. 1947; 12: 617
• 21 Tafelska-Kaczmarek A, Prewysz-Kwinto A, Skowerski K, Pietrasiak K, Kozakiewicz A, Zaidlewicz M. Tetrahedron: Asymmetry 2010; 21: 2244
• 22 Lu C, Luo Z, Huang L, Li X. Tetrahedron: Asymmetry 2011; 22: 722