Recent Advances in the Enantioselective Oxidative α-C–H Functionalization of Amines

Ming-Xing Cheng; Shang-Dong Yang

doi:10.1055/s-0036-1588342

Synlett, Table of Contents

Synlett 2017; 28(02): 159-174
DOI: 10.1055/s-0036-1588342

account

Recent Advances in the Enantioselective Oxidative α-C–H Functionalization of Amines

Authors

Ming-Xing Cheng

^aState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China.
Shang-Dong Yang*

^aState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China.

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. China., Email: yangshd@lzu.edu.cn

Abstract

All articles of this category

Abstract

Cross-dehydrogenative coupling (CDC) has emerged as a powerful synthetic method for the straightforward and efficient construction of C–C and C–heteroatom bonds. In particular, asymmetric versions of this reaction are highly desirable, since they would provide a simple approach to complex molecules from simple materials without any prefunctionalization of substrates. In recent years, great achievements have been made in this area, and many powerful approaches have been developed for this transformation with high enantioselectivity. In this account, we summarize recent advances in the enantioselective oxidative α-C(sp³)–H bond functionalization of amines according to the catalytic reaction systems. Moreover, the catalytic mechanisms of the asymmetric oxidative reactions are also discussed.

1 Introduction

2 Transition-Metal-Catalyzed Enantioselective Oxidative C–H Functionalization

3 Organocatalytic Enantioselective Oxidative C–H Functionalization

4 Photoredox Catalytic Enantioselective Oxidative C–H Functionalization

5 Conclusions

Key words

cross-dehydrogenative coupling - amines - asymmetric synthesis - oxidative C–H functionalization

Full Text

References

References

1a Dyker G. Handbook of C–H Transformations . Wiley-VCH; Weinheim: 2005
1b Yu J.-Q, Shi Z.-J In C–H Activation: Topics in Current Chemistry . Springer; Berlin: 2010

Selected recent reviews on oxidative C–H functionalization:

2a Scheuermann CJ. Chem. Asian J. 2010; 5: 436
2b Klussmann M, Sureshkumar D. Synthesis 2011; 353
2c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
2d Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
2e Rohlmann R, Mancheño OG. Synlett 2013; 24: 6
2f Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
2g Narayan R, Matcha K, Antonchick AP. Chem. Eur. J. 2015; 21: 14678
2h Stockerl S, Mancheño OG. Org. Chem. Front. 2016; 3: 277

For example see:

3a Li C.-J. Acc. Chem. Res. 2009; 42: 335
3b Li Z, Bohle D, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 8928
3c Catino AJ, Nichols JM, Nettles BJ, Doyle MP. J. Am. Chem. Soc. 2006; 128: 5648
3d Murahashi S.-I, Komiya N, Terai H. Angew. Chem. Int. Ed. 2005; 44: 6931
3e Murahashi S.-I, Nakae T, Terai H, Komiya N. J. Am. Chem. Soc. 2008; 130: 11005
3f Condie AG, González-Gómez JC, Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464
3g Xie J, Huang Z.-Z. Angew. Chem. Int. Ed. 2010; 49: 10181
3h Xie J, Li H, Zhou J, Cheng Y, Zhu C. Angew. Chem. Int. Ed. 2012; 51: 1252
3i Li C.-J, Li Z. Pure Appl. Chem. 2006; 78: 953

For recent CDC reactions of tertiary amines see:

4a Xie Z, Liu L, Chen W, Zheng H, Xu Q, Yuan H, Lou H. Angew. Chem. Int. Ed. 2014; 53: 3904
4b Chu L, Qing F. Chem. Commun. 2010; 46: 6285
4c Ghobrial M, Harhammer K, Mihovilovic MD, Schnürch M. Chem. Commun. 2010; 46: 8836
4d Sundararaju B, Achard M, Sharma GV. M, Bruneau C. J. Am. Chem. Soc. 2011; 133: 10340
4e Liu X, Sun B, Xie Z, Qin X, Liu L, Lou H. J. Org. Chem. 2013; 78: 3104

For representative recent reviews see:

5a Bentley KW. Nat. Prod. Rep. 2005; 22: 249
5b Bentley KW. Nat. Prod. Rep. 2004; 21: 395

6 Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
7 Li Z, Li C.-J. Org. Lett. 2004; 6: 4997
8 Li Z, MacLeo PD, Li C.-J. Tetrahedron: Asymmetry 2006; 17: 590
9 Li Z, Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810

10a Wei C, Li C.-J. J. Am. Chem. Soc. 2002; 124: 5638
10b Wei C, Mague JT, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5749

11a Gommermann N, Koradin C, Polborn K, Knochel P. Angew. Chem. Int. Ed. 2003; 42: 5763
11b Koradin C, Polborn K, Knochel P. Angew. Chem. Int. Ed. 2002; 41: 2535

12 Yu J, Li Z, Jia K, Jiang Z, Liu M, Su W. Tetrahedron Lett. 2013; 54: 2006
13 Sun S, Li C, Floreancig PE, Lou H, Liu L. Org. Lett. 2015; 17: 1684

14a Brossi A, Teitel S. Helv. Chim. Acta 1969; 52: 1228
14b Tietze LF, Rackelmann N, Müller I. Chem. Eur. J. 2004; 10: 2722

15a Sasamoto N, Dubs C, Hamashima Y, Sodeoka M. J. Am. Chem. Soc. 2006; 128: 14010
15b Christian D, Yoshitaka H, Naoki S, Seidel TM, Suzuki S, Hashizume D, Sodeoka M. J. Org. Chem. 2008; 73: 5859

16 Zhang G, Ma Y, Wang S, Zhang Y, Wang R. J. Am. Chem. Soc. 2012; 134: 12334
17 Zhang J, Tiwari B, Xing C, Chen X, Chi YR. Angew. Chem. Int. Ed. 2012; 51: 3649

18a Leonard NJ, Leubner GW. J. Am. Chem. Soc. 1949; 71: 3408
18b Murahashi S.-I, Komiya N, Terai H. Angew. Chem. Int. Ed. 2005; 44: 6931

19a Beak P, Zajdel WJ, Reitz DB. Chem. Rev. 1984; 84: 471
19b Maruoka K, Ooi T. Chem. Rev. 2003; 103: 3013

20 Zhang G, Zhang Y, Wang R. Angew. Chem. Int. Ed. 2011; 50: 10429
21 Wei X.-H, Wang G.-W, Yang S.-D. Chem. Commun. 2015; 51: 832
22 Tan Y, Yuan W, Gong L, Meggers E. Angew. Chem. Int. Ed. 2015; 54: 13045
23 Xie Z, Liu X, Liu L. Org. Lett. 2016; 18: 2982
24 Zhang G, Ma Y, Wang S, Kong W, Wang R. Chem. Sci. 2013; 4: 2645
25 Neel AJ, Hehn JP, Tripet PF, Toste FD. J. Am. Chem. Soc. 2013; 135: 14044
26 Ma Y, Zhang G, Zhang J, Yang D, Wang R. Org. Lett. 2014; 16: 5358

27a For bifunctional catalyst see: Matsunaga S, Ohshima T, Shibasaki M. Adv. Synth. Catal. 2002; 344: 3
27b Shibasaki M, Kanai M. Chem. Pharm. Bull. 2001; 49: 511
27c Rowlands GJ. Tetrahedron 2001; 57: 1865
27d Gröger H. Chem. Eur. J. 2001; 7: 5247
27e Shibasaki M, Sasai H, Arai T. Angew. Chem., Int. Ed. Engl. 1997; 36: 1236
27f Shibasaki M, Kanai M, Funabashi K. Chem. Commun. 2002; 1989
27g Shibasaki M. Chemtracts: Org. Chem. 1999; 12: 979
27h Shibasaki M. Enantiomer 1999; 4: 513
27i Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047

28 Liu X, Meng Z, Li C, Lou H, Liu L. Angew. Chem. Int. Ed. 2015; 54: 6012
29 Liu X, Sun S, Meng Z, Lou H, Liu L. Org. Lett. 2015; 17: 2396
30 Cheng M.-X, Ma R.-S, Yang Q, Yang S.-D. Org. Lett. 2016; 18: 3262
31 Xie Z, Zan Z, Sun S, Pan X, Liu L. Org. Lett. 2016; 18: 3944

32a Kang YK, Kim SM, Kim DY. J. Am. Chem. Soc. 2010; 132: 11874
32b Mori K, Ehara K, Kurihara K, Akiyama T. J. Am. Chem. Soc. 2011; 133: 6166

33a Suh CW, Woo SB, Kim DY. Asian J. Org. Chem. 2014; 3: 399
33b Suh CW, Kim DY. Org. Lett. 2014; 16: 5374

34 Kang YK, Kim DY. Chem. Commun. 2014; 50: 222

35a Ghislieri D, Green AP, Pontini M, Willies SC, Rowles I, Frank A, Grogan G, Turner NJ. J. Am. Chem. Soc. 2013; 135: 10863
35b Graaff CD, Oppelaar B, Péruch O, Velde CM. L. V, Bechi B, Turner NJ, Ruijter E, Orru RV. A. Adv. Synth. Catal. 2016; 358: 1555

36 Köhler V, Bailey KR, Znabet A, Raftery J, Helliwell M, Turner NJ. Angew. Chem. Int. Ed. 2010; 49: 2182

37a Nicewicz D, MacMillan DW. C. Science 2008; 322: 77
37b Shih H.-W, Vander Wal MN, Grange RL, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 13600
37c Nagib DA, Scott ME, MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 10875

38a Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
38b Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
38c Du J, Skubi KL, Schultz DM, Yoon TP. Science 2014; 344: 392

39a Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
39b Sanford MS, Ye Y. J. Am. Chem. Soc. 2012; 134: 9034

40 Rueping M, Koenigs RM, Poscharny K, Fabry DC, Leonori D, Vila C. Chem. Eur. J. 2012; 18: 5170
41 DiRocco DA, Rovis T. J. Am. Chem. Soc. 2012; 134: 8094
42 Bergonzini G, Schindler CS, Wallentin C.-J, Jacobsen EN, Stephenson CR. J. Chem. Sci. 2014; 5: 112
43 Perepichka I, Kundu S, Hearne Z, Li C.-J. Org. Biomol. Chem. 2015; 13: 447
44 Wei G, Zhang C, Bures F, Ye X, Tan C.-H, Jiang Z. ACS. Catal. 2016; 6: 3708