Catalytic, Enantioselective Diamination of Alkenes

Enantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area.

1 Introduction

2 Cycloaddition Pathway

3 Two-Electron Redox Pathway

3.1 Pd(0)/Pd(II) Diamination

3.2 Pd(II)/Pd(IV) Diamination

3.3 I(I)/I(III) Diamination

3.4 Se(II)/Se(IV) Diamination

4 One-Electron Radical Pathway

4.1 Cu-Catalyzed Diamination

4.2 Fe-Catalyzed Diamination

5 Summary and Outlook

Key words

vicinal diamines - asymmetric catalysis - redox catalysis - olefin diamination - transition metal - radical

Volltext

Referenzen

References

1a Michalson ET, Szmuszkovicz J. Prog. Drug Res. 1989; 33: 135
1b Lucet D, Le Gall T, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
1c Viso A, Fernández de la Pradilla R, García A, Flores A. Chem. Rev. 2005; 105: 3167
1d Kotti SR. S. S, Timmons C, Li G. Chem. Biol. Drug Des. 2006; 67: 101
1e Kizirian J.-C. Chem. Rev. 2008; 108: 140
1f Cardona F, Goti A. Nat. Chem. 2009; 1: 269
1g de Figueiredo RM. Angew. Chem. Int. Ed. 2009; 48: 1190
1h Grygorenko OO, Radchenko DS, Volochnyuk DM, Tolmachev AA, Komarov IV. Chem. Rev. 2011; 111: 5506
1i Viso A, Fernández de laPradilla R, Tortosa M, García A, Flores A. Chem. Rev. 2011; 111: PR1
1j De Jong S, Nosal DG, Wardrop DJ. Tetrahedron 2012; 68: 4067
1k Muñiz K, Martínez C. J. Org. Chem. 2013; 78: 2168
1l Zhu Y, Cornwall RG, Du H, Zhao B, Shi Y. Acc. Chem. Res. 2014; 47: 3665
1m Zhang X, You S.-L. Chem 2017; 3: 919
1n Parry JB, Fu N, Lin S. Synlett 2018; 29: 257
1o Wu Z, Hu M, Li J, Wu W, Jiang H. Org. Biomol. Chem. 2021; 19: 3036

2 Marquet A. Pure Appl. Chem. 1993; 65: 1249
3 McGregor DN. Penicillins . In Comprehensive Heterocyclic Chemistry, Chap.5.11. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 299

4a Gardiner RA, Rinehart KL, Snyder JJ, Broquist HP. J. Am. Chem. Soc. 1968; 90: 5639
4b Rinehart KL, Cartwright D, Gardiner RA. J. Am. Chem. Soc. 1970; 92: 7615

5a Rosenberg B, Vancamp L, Trosko JE, Mansour VH. Nature 1969; 222: 385
5b Pasini A, Zunino F. Angew. Chem., Int. Ed. Engl. 1987; 26: 615
5c Reedijk J. Chem. Commun. 1996; 801

6a Shibasaki M, Kanai M. Eur. J. Org. Chem. 2008; 1839
6b Magano J. Tetrahedron 2011; 67: 7875
6c Shibasaki M, Kanai M, Yamatsugu K. Isr. J. Chem. 2011; 51: 316

7 Bodurow CC, Boyer BD, Brennan J, Bunnell CA, Burks JE, Carr MA, Doecke CW, Eckrich TM, Fisher JW, Gardner JP, Graves BJ, Hines P, Hoying RC, Jackson BG, Kinnick MD, Kochert CD, Lewis JS, Luke WD, Moore LL, Morin JM, Nist RL, Prather DE, Sparks DL, Vladuchick WC. Tetrahedron Lett. 1989; 30: 2321
8 Duffy RA, Morgan C, Naylor R, Higgins GA, Varty GB, Lachowicz JE, Parker EM. Pharmacol. Biochem. Behav. 2012; 102: 95
9 Magano J. Chem. Rev. 2009; 109: 4398

10a Corey EJ, Imwinkelried R, Pikul S, Xiang YB. J. Am. Chem. Soc. 1989; 111: 5493
10b Corey EJ, Yu CM, Kim SS. J. Am. Chem. Soc. 1989; 111: 5495
10c Corey EJ, Kim SS. J. Am. Chem. Soc. 1990; 112: 4976

11a Kubota K, Leighton JL. Angew. Chem. Int. Ed. 2003; 42: 946
11b Burns NZ, Hackman BM, Ng PY, Powelson IA, Leighton JL. Angew. Chem. Int. Ed. 2006; 45: 3811
11c Kim H, Ho S, Leighton JL. J. Am. Chem. Soc. 2011; 133: 6517
11d Chalifoux WA, Reznik SK, Leighton JL. Nature 2012; 487: 86

12a Basak AK, Shimada N, Bow WF, Vicic DA, Tius MA. J. Am. Chem. Soc. 2010; 132: 8266
12b Yu F, Jin Z, Huang H, Ye T, Liang X, Ye J. Org. Biomol. Chem. 2010; 8: 4767
12c Zhang L, Fu N, Luo S. Acc. Chem. Res. 2015; 48: 986
12d Simon A, Lam Y.-h, Houk KN. J. Am. Chem. Soc. 2016; 138: 503
12e Wang P, Li H.-F, Zhao J.-Z, Du Z.-H, Da C.-S. Org. Lett. 2017; 19: 2634

13a Tomioka K. Synthesis 1990; 541
13b Zhang W, Loebach JL, Wilson SR, Jacobsen EN. J. Am. Chem. Soc. 1990; 112: 2801
13c Jacobsen EN, Zhang W, Muci AR, Ecker JR, Deng L. J. Am. Chem. Soc. 1991; 113: 7063
13d Zhang W, Jacobsen EN. J. Org. Chem. 1991; 56: 2296
13e Noyori R, Hashiguchi S. Acc. Chem. Res. 1997; 30: 97
13f Seiders TJ, Ward DW, Grubbs RH. Org. Lett. 2001; 3: 3225
13g Saito B, Fu GC. J. Am. Chem. Soc. 2008; 130: 6694
13h Owston NA, Fu GC. J. Am. Chem. Soc. 2010; 132: 11908
13i Lu Z, Wilsily A, Fu GC. J. Am. Chem. Soc. 2011; 133: 8154
13j Wilsily A, Tramutola F, Owston NA, Fu GC. J. Am. Chem. Soc. 2012; 134: 5794
13k Cong H, Fu GC. J. Am. Chem. Soc. 2014; 136: 3788
13l Deshpande SH, Shende VS, Shingote SK, Chakravarty D, Puranik VG, Chaudhari RV, Kelkar AA. RSC Adv. 2015; 5: 51722
13m Janssen-Müller D, Schlepphorst C, Glorius F. Chem. Soc. Rev. 2017; 46: 4845
13n Shen P.-X, Hu L, Shao Q, Hong K, Yu J.-Q. J. Am. Chem. Soc. 2018; 140: 6545

14a Pikul S, Corey EJ. Org. Synth. 1993; 71: 30
14b Alexakis A, Aujard I, Kanger T, Mangeney P. Org. Synth. 1999; 76: 23

15a Waki M, Kitajima Y, Izumiya N. Synthesis 1981; 266
15b Baldwin JE, Adlington RM, Birch DJ. Tetrahedron Lett. 1985; 26: 5931

16a Urban S, Ortega N, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 3803
16b Zhang Z, Du H. Angew. Chem. Int. Ed. 2015; 54: 623
16c Ma W, Zhang J, Xu C, Chen F, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2016; 55: 12891
16d Chen Y, Pan Y, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2019; 58: 16831

17a Arrayás RG, Carretero JC. Chem. Soc. Rev. 2009; 38: 1940
17b Marqués-López E, Merino P, Tejero T, Herrera RP. Eur. J. Org. Chem. 2009; 2401
17c Noble A, Anderson JC. Chem. Rev. 2013; 113: 2887
17d Uraguchi D, Kinoshita N, Kizu T, Ooi T. J. Am. Chem. Soc. 2015; 137: 13768
17e Chen J, Gong X, Li J, Li Y, Ma J, Hou C, Zhao G, Yuan W, Zhao B. Science 2018; 360: 1438
17f Shao X, Li K, Malcolmson SJ. J. Am. Chem. Soc. 2018; 140: 7083

18a Zhou M, Li K, Chen D, Xu R, Xu G, Tang W. J. Am. Chem. Soc. 2020; 142: 10337
18b For reductive coupling of imines and allenamides, see: Agrawal T, Martin RT, Collins S, Wilhelm A, Edwards MD, Gutierrez O, Sieber JD. J. Org. Chem. 2021; 86: 5026

19a Cho Y.-h, Zunic V, Senboku H, Olsen M, Lautens M. J. Am. Chem. Soc. 2006; 128: 6837
19b MacDonald MJ, Schipper DJ, Ng PJ, Moran J, Beauchemin AM. J. Am. Chem. Soc. 2011; 133: 20100
19c Garlets ZJ, Parenti KR, Wolfe JP. Chem. Eur. J. 2016; 22: 5919
19d Struble TJ, Lankswert HM, Pink M, Johnston JN. ACS Catal. 2018; 8: 11926
19e Ichikawa S, Dai X.-J, Buchwald SL. Org. Lett. 2019; 21: 4370
19f Vanable EP, Kennemur JL, Joyce LA, Ruck RT, Schultz DM, Hull KL. J. Am. Chem. Soc. 2019; 141: 739

20a Dumoulin A, Lalli C, Retailleau P, Masson G. Chem. Commun. 2015; 51: 5383
20b Dumoulin A, Bernadat G, Masson G. J. Org. Chem. 2017; 82: 1775
20c Yu L, Somfai P. Angew. Chem. Int. Ed. 2019; 58: 8551

21a Lang K, Torker S, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2019; 141: 12388
21b Yang Y, Cho I, Qi X, Liu P, Arnold FH. Nat. Chem. 2019; 11: 987
21c Zhou Z, Tan Y, Yamahira T, Ivlev S, Xie X, Riedel R, Hemming M, Kimura M, Meggers E. Chem 2020; 6: 2024
21d Nie X, Yan Z, Ivlev S, Meggers E. J. Org. Chem. 2021; 86: 750

22a Fukuta Y, Mita T, Fukuda N, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2006; 128: 6312
22b Arai K, Lucarini S, Salter MM, Ohta K, Yamashita Y, Kobayashi S. J. Am. Chem. Soc. 2007; 129: 8103
22c Wu B, Gallucci JC, Parquette JR, RajanBabu TV. Chem. Sci. 2014; 5: 1102
22d Chai Z, Yang P.-J, Zhang H, Wang S, Yang G. Angew. Chem. Int. Ed. 2017; 56: 650

23a Muñiz K, Nieger M. Synlett 2003; 211
23b Muñiz K, Nieger M, Mansikkamäki H. Angew. Chem. Int. Ed. 2003; 42: 5958
23c Muñiz K. Chem. Soc. Rev. 2004; 33: 166
23d Muñiz K. New J. Chem. 2005; 29: 1371
23e Muñiz K, Nieger M. Chem. Commun. 2005; 2729
23f Almodovar I, Hövelmann CH, Streuff J, Nieger M, Muñiz K. Eur. J. Org. Chem. 2006; 704

24a Du H, Yuan W, Zhao B, Shi Y. J. Am. Chem. Soc. 2007; 129: 11688
24b Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2007; 129: 762
24c Du H, Zhao B, Shi Y. Org. Synth. 2009; 86: 315

25a Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2008; 130: 8590
25b Zhao B, Du H, Fu R, Shi Y. Org. Synth. 2010; 87: 263

26 Xu L, Shi Y. J. Org. Chem. 2008; 73: 749
27 Cornwall RG, Zhao B, Shi Y. Org. Lett. 2013; 15: 796
28 Wu M.-S, Fan T, Chen S.-S, Han Z.-Y, Gong L.-Z. Org. Lett. 2018; 20: 2485
29 Streuff J, Hövelmann CH, Nieger M, Muñiz K. J. Am. Chem. Soc. 2005; 127: 14586
30 Ingalls EL, Sibbald PA, Kaminsky W, Michael FE. J. Am. Chem. Soc. 2013; 135: 8854
31 Li X, Qi X, Hou C, Chen P, Liu G. Angew. Chem. Int. Ed. 2020; 59: 17239
32 Liu X, Hou C, Peng Y, Chen P, Liu G. Org. Lett. 2020; 22: 9371

33a Flores A, Cots E, Bergès J, Muñiz K. Adv. Synth. Catal. 2019; 361: 2
33b Parra A. Chem. Rev. 2019; 119: 12033
33c Hypervalent Iodine Chemistry . In Topics in Current Chemistry, Vol. 373. Wirth T. Springer; Switzerland: 2016
33d Zhdankin VV. Hypervalent Iodine Chemistry . John Wiley & Sons; Chichester: 2014

34 Röben C, Souto JA, González Y, Lishchynskyi A, Muñiz K. Angew. Chem. Int. Ed. 2011; 50: 9478
35 Cresswell AJ, Eey ST. C, Denmark SE. Angew. Chem. Int. Ed. 2015; 54: 15642
36 Mizar P, Laverny A, El-Sherbini M, Farid U, Brown M, Malmedy F, Wirth T. Chem. Eur. J. 2014; 20: 9910

37a Muñiz K, Barreiro L, Romero RM, Martínez C. J. Am. Chem. Soc. 2017; 139: 4354
37b Muñiz K. Acc. Chem. Res. 2018; 51: 1507

38a Freudendahl DM, Santoro S, Shahzad SA, Santi C, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 8409
38b Claudio S, Stefano S, Benedetta B. Curr. Org. Chem. 2010; 14: 2442
38c Breder A, Ortges S. Tetrahedron Lett. 2015; 56: 2843
38d Singh FV, Wirth T. Organoselenium Chemistry, Chap. 8. Wirth T. Wiley-VCH; Weinheim: 2012
38e Rathore V, Jose C, Kumar S. New J. Chem. 2019; 43: 8852
38f Shao L, Li Y, Lu J, Jiang X. Org. Chem. Front. 2019; 6: 2999

39a Cresswell AJ, Eey ST. C, Denmark SE. Nat. Chem. 2015; 7: 146
39b Gilbert BB, Eey ST. C, Ryabchuk P, Garry O, Denmark SE. Tetrahedron 2019; 75: 4086

40 Tao Z, Gilbert BB, Denmark SE. J. Am. Chem. Soc. 2019; 141: 19161

41a Wang F, Chen P, Liu G. Acc. Chem. Res. 2018; 51: 2036
41b Wang K, Kong W. Chin. J. Chem. 2018; 36: 247
41c Gu Q.-S, Li Z.-L, Liu X.-Y. Acc. Chem. Res. 2020; 53: 170
41d Li Z.-L, Fang G.-C, Gu Q.-S, Liu X.-Y. Chem. Soc. Rev. 2020; 49: 32

42 Du H, Zhao B, Yuan W, Shi Y. Org. Lett. 2008; 10: 4231
43 Zhao B, Du H, Shi Y. J. Org. Chem. 2009; 74: 8392

44a Sequeira FC, Turnpenny BW, Chemler SR. Angew. Chem. Int. Ed. 2010; 49: 6365
44b Turnpenny BW, Chemler SR. Chem. Sci. 2014; 5: 1786

45 Fu S, Yang H, Li G, Deng Y, Jiang H, Zeng W. Org. Lett. 2015; 17: 1018
46 Wang F.-L, Dong X.-Y, Lin J.-S, Zeng Y, Jiao G.-Y, Gu Q.-S, Guo X.-Q, Ma C.-L, Liu X.-Y. Chem 2017; 3: 979
47 Yuan Y.-A, Lu D.-F, Chen Y.-R, Xu H. Angew. Chem. Int. Ed. 2016; 55: 534
48 Lv D, Sun Q, Zhou H, Ge L, Qu Y, Li T, Ma X, Li Y, Bao H. Angew. Chem. Int. Ed. 2021; 60: 12455

49a Tabor JR, Obenschain DC, Michael FE. Chem. Sci. 2020; 11: 1677
49b Minakata S, Miwa H, Yamamoto K, Hirayama A, Okumura S. J. Am. Chem. Soc. 2021; 143: 4112

50 Makai S, Falk E, Morandi B. J. Am. Chem. Soc. 2020; 142: 21548