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

Ming-Lei Yuan; Jian-Hua Xie; Xiao-Hui Yang; Qi-Lin Zhou

doi:10.1055/s-0034-1378891

Synthesis, Table of Contents

Synthesis 2014; 46(21): 2910-2916
DOI: 10.1055/s-0034-1378891

paper

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

Ming-Lei Yuan

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China Fax: +86(22)23506177 Email: jhxie@nankai.edu.cn Email: qlzhou@nankai.edu.cn

,

Jian-Hua Xie*

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China Fax: +86(22)23506177 Email: jhxie@nankai.edu.cn Email: qlzhou@nankai.edu.cn

,

Xiao-Hui Yang

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China Fax: +86(22)23506177 Email: jhxie@nankai.edu.cn Email: qlzhou@nankai.edu.cn

,

Qi-Lin Zhou*

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China Fax: +86(22)23506177 Email: jhxie@nankai.edu.cn Email: qlzhou@nankai.edu.cn

› Author Affiliations

Abstract

All articles of this category

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

Full Text

References

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

Supplementary Material

Supporting Information