Transition-Metal-Catalyzed Enantioselective Synthesis of Indoles from 2-Alkynylanilines

Zhi-Shi Ye; Jin-Chen Li; Gang Wang

doi:10.1055/a-1729-9572

Synthesis, Table of Contents

Synthesis 2022; 54(09): 2133-2147
DOI: 10.1055/a-1729-9572

short review

Transition-Metal-Catalyzed Enantioselective Synthesis of Indoles from 2-Alkynylanilines

Zhi-Shi Ye ∗

,

Jin-Chen Li

,

Gang Wang

Abstract

All articles of this category

Abstract

Optically active indole derivatives are ubiquitous in natural products and are widely recognized as privileged components in pharmacologically relevant compounds. Therefore, developing catalytic asymmetric approaches for constructing indole derivatives is highly desirable. In this short review, we summarize methods for the transition-metal-catalyzed enantioselective synthesis of indoles from 2-alkynylanilines.

1 Introduction

2 Aminometalation-Triggered Asymmetric Cross-Coupling Reactions/Insertion

2.1 Asymmetric Cross-Coupling Reactions

2.2 Asymmetric Insertion of C=O, C=C and C≡N Bonds

3 Asymmetric Relay Catalysis

4 Conclusion

Key words

indoles - 2-alkynylanilines - aminometalation - cross-coupling - insertion - relay catalysis - axial chirality

Full Text

References

References

1a Taylor WI. Indole Alkaloids . Pergamon Press; Oxford: 1966
1b Pritchett BP, Stoltz BM. Nat. Prod. Rep. 2018; 35: 559
1c Wang J.-J, Shen Y.-K, Hu W.-P, Hsieh M.-C, Lin F.-L, Hsu M.-K, Hsu M.-H. J. Med. Chem. 2006; 49: 1442
1d Yamamoto Y, Kurazono M. Bioorg. Med. Chem. Lett. 2007; 17: 1626
1e Gurkan-Alp AS, Mumcuoglu M, Andac CA, Dayanc E, Cetin-Atalay R, Buyukbingol E. Eur. J. Med. Chem. 2012; 58: 346
1f Zhuang S.-H, Lin Y.-C, Chou L.-C, Hsu M.-H, Lin H.-Y, Huang C.-H, Lien J.-C, Kuo S.-C, Huang L.-J. Eur. J. Med. Chem. 2013; 66: 466
1g Hwang D.-J, Wang J, Li W, Miller DD. ACS Med. Chem. Lett. 2015; 6: 993
1h Sherer C, Snape TJ. Eur. J. Med. Chem. 2015; 97: 552
1i Zhang M.-Z, Jia C.-Y, Gu Y.-C, Mulholland N, Turner S, Beattie D, Zhang W.-H, Yang G.-F, Clough J. Eur. J. Med. Chem. 2017; 126: 669

2 Chen J, Chen J.-J, Yao X, Gao K. Org. Biomol. Chem. 2011; 9: 5334

3a Saxton JE. In The Alkaloids, Vol. 51, Chap. 1. Cordell GA. Academic Press; New York: 1998
3b Blair LM, Calvert MB, Gaich T, Lindel T, Phaffenbach M, Sperry J. In The Alkaloids: Chemistry and Biology, Vol. 77. Knölker H.-J. Academic Press; Cambridge: 2017

4 Zhao N, Li L, Liu J.-H, Zhuang P.-Y, Yu S.-S, Ma S.-G, Qu J, Chen N.-H, Wu L.-J. Tetrahedron 2012; 68: 3288
5 Meng D, Li H, Yang M, Ruiz MD. L, Dewnani SV, Jian T, Parker DL. J, Zhang T, Campeau L.-C, Harper B, Wood HB, Xu J, Berger R, Wu JY, Orr RK, Walsh SP. WO2016133793A1, 2016
6 Mihalic JT, Chen X.-Q, Fan P.-C, Chen X, Fu Y, Liang L.-L, Reed M, Tang L, Chen J.-L, Jaen J, Li L, Dai K. Bioorg. Med. Chem. Lett. 2011; 21: 7001
7 Norton RS, Wells RJ. J. Am. Chem. Soc. 1982; 104: 3628
8 Baumann T, Brückner R. Angew. Chem. Int. Ed. 2019; 58: 4714

9a Kondo Y, Kojima S, Sakamoto T. J. Org. Chem. 1997; 62: 6507
9b Ma C, Liu X, Li X, Flippen-Anderson J, Yu S, Cook JM. J. Org. Chem. 2001; 66: 4525
9c Kamijo S, Sasaki Y, Yamamoto Y. Tetrahedron Lett. 2004; 45: 35

10a Krüger K, Tillack A, Beller M. Adv. Synth. Catal. 2008; 350: 2153
10b Li J.-X, Yang S.-R, Wu W.-Q, Jiang H.-F. Chem. Asian J. 2019; 14: 4114
10c Platon M, Amardeil R, Djakovitch L, Hierso J.-C. Chem. Soc. Rev. 2012; 41: 3929
10d Sebastião J, Neto S, Zeni G. Org. Chem. Front. 2020; 7: 155
10e Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
10f Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875

11 Taylor EC, Katz AH, Salgado-Zamora H, McKillop A. Tetrahedron Lett. 1985; 26: 5963
12 Sakamoto T, Kondo Y, Iwashita S, Nagano T, Yamanaka H. Chem. Pharm. Bull. 1988; 36: 1305
13 Kondo Y, Shiga F, Murata N, Sakamoto T, Yamanaka H. Tetrahedron 1994; 50: 11803

14a Arcadia A, Cacchi S, Marinelli F. Tetrahedron Lett. 1992; 33: 3915
14b Cacchi S, Fabrizi G, Goggiamani A. Adv. Synth. Catal. 2006; 348: 1301

15 Trost B, McClory A. Angew. Chem. Int. Ed. 2007; 46: 2074
16 Li X.-W, Chianese AR, Vogel T, Crabtree RH. Org. Lett. 2005; 7: 5437
17 Iritani K, Matsubara S, Utimoto K. Tetrahedron Lett. 1988; 29: 1799
18 Rodriguez AL, Koradin C, Dohle W, Knochel P. Angew. Chem. Int. Ed. 2000; 39: 2488

19a Cui Y.-M, Lin Y, Xu L.-W. Coord. Chem. Rev. 2017; 330: 37
19b Kumarasamy E, Raghunathan R, Sibi MP, Sivaguru J. Chem. Rev. 2015; 115: 11239
19c Smyth JE, Butler NM, Keller PA. Nat. Prod. Rep. 2015; 32: 1562
19d Privileged Chiral Ligands and Catalysts . Zhou Q.-L. Wiley-VCH; Weinheim: 2011
19e Toenjes ST, Gustafson JL. Future Med. Chem. 2018; 10: 409

For examples, see:

20a Ito C, Thoyama Y, Omura M, Kajiura I, Furukawa H. Chem. Pharm. Bull. 1993; 41: 2096
20b Bringmann G, Tasler S, Endress H, Kraus J, Messer K, Wohlfarth M, Lobin W. J. Am. Chem. Soc. 2001; 123: 2703
20c Bringmann G, Tasler S. Tetrahedron 2001; 57: 331
20d Berens U, Brown JM, Long J, Selke R. Tetrahedron: Asymmetry 1996; 7: 285
20e Anilkumar GN, Lesburg CA, Selyutin O, Rosenblum SB, Zeng Q, Jiang Y, Chan T.-Y, Pu H, Vaccaro H, Wang L, Bennett F, Chen KX, Duca J, Gavalas S, Huang Y, Pinto P, Sannigrahi M, Velazquez F, Venkatraman S, Vibulbhan B, Agrawal S, Butkiewicz N, Feld B, Ferrari E, He Z, Jiang C.-k, Palermo RE, Mcmonagle P, Huang H.-C, Shih N.-Y, Njoroge G, Kozlowski JA. Bioorg. Med. Chem. Lett. 2011; 21: 5336
20f Luz JG, Carson MW, Condon B, Clawson D, Pustilnik A, Kohlman DT, Barr RJ, Bean JS, Dill MJ, Sindelar DK, Maletic M, Coghlan MJ. J. Med. Chem. 2015; 58: 6607
20g Mino T, Komatsu S, Wakui K, Yamada H, Saotome H, Sakamoto M, Fujita T. Tetrahedron: Asymmetry 2010; 21: 711

21a Ototake N, Morimoto Y, Mokuya A, Fukaya H, Shida Y, Kitagawa O. Chem. Eur. J. 2010; 16: 6752
21b Morimoto Y, Shimizu S, Mokuya A, Ototake N, Saito A, Kitagawa O. Tetrahedron 2016; 72: 5221

22a Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
22b Li T.-Z, Liu S.-J, Tan W, Shi F. Chem. Eur. J. 2020; 26: 15779
22c Kitagawa O. Acc. Chem. Res. 2021; 54: 719
22d Cheng JK, Xiang S.-H, Li S, Ye L, Tan B. Chem. Rev. 2021; 121: 4805
22e Corti V, Bertuzzi G. Synthesis 2020; 52: 2450

For selected reviews on the transition-metal-catalyzed formation of heterocyclic compounds, see:

23a Alonso F, Beletskaya IP, Yus M. Chem. Rev. 2004; 104: 3079
23b Hartwig JF. Organotransition Metal Chemistry: From Bonding to Catalysis . University Science Books; Mill Valley (CA, USA): 2010
23c Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, 2nd ed. Beller M, Bolm C. Wiley-VCH; Weinheim: 2004
23d Tsuji J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis. John Wiley & Sons; New York: 2000

24 He Y.-P, Wu H, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2020; 59: 2105

25a Djafri A, Roussel C, Sandström J. J. Chem. Soc., Perkin Trans. 2 1985; 273
25b Zhang S, Yao Q.-J, Liao G, Li X, Li H, Chen H.-M, Hong X, Shi B.-F. ACS Catal. 2019; 9: 1956

26 Tian M, Bai D, Zheng G, Chang J, Li X. J. Am. Chem. Soc. 2019; 141: 9527
27 Li X, Zhao L, Qi Z, Li X. Org. Lett. 2021; 23: 5901
28 Wang C.-S, Wei L, Fu C, Wang X.-H, Wang C.-J. Org. Lett. 2021; 23: 7401
29 Yang W.-C, Chen X.-B, Song K.-L, Wu B, Gan W.-E, Zheng Z.-J, Cao J, Xu L.-W. Org. Lett. 2021; 23: 1309
30 Sun Y.-L, Wang X.-B, Sun F.-N, Chen Q.-Q, Cao J, Xu Z, Xu L.-W. Angew. Chem. Int. Ed. 2019; 58: 6747

31a Liu Y.-L, Lin X.-Y. Adv. Synth. Catal. 2019; 361: 876
31b Manabu H, Takashi M, Kazuaki I. Curr. Org. Chem. 2007; 11: 127
31c Pu L, Yu H.-B. Chem. Rev. 2001; 101: 757
31d Gbubele JD, Olszewski TK. Org. Biomol. Chem. 2021; 19: 2823

32 Chen J, Han X, Lu X. J. Org. Chem. 2017; 82: 1977
33 Chen J, Han X, Lu X. Org. Lett. 2018; 20: 7470

For selected developed drugs with a hydropyrano[3,4-b]indole skeleton, see:

34a Demerson CA, Abraham NA, Schilling G, Martel RR, Asciak CJ. J. Med. Chem. 1983; 26: 1778
34b LaPorte MG, Draper TL, Miller LE. Bioorg Med. Chem. Lett. 2010; 20: 2968
34c Schunk S, Linz K, Frormann S, Hinze C, Oberbörsch S, Sundermann B, Zemolka S, Englberger W, Germann T, Christoph T, Kögel B.-Y, Schröder W, Harlfinger S, Saunders D, Kless A, Schick H, Sonnenschein H. ACS Med. Chem. Lett. 2014; 5: 851

35a Larghi EL, Kaufman TS. Eur. J. Org. Chem. 2011; 27: 5195
35b Lombardo VM, Thomas CD, Scheidt KA. Angew. Chem. Int. Ed. 2013; 52: 12910
35c Ascic E, Ohm RG, Petersen R, Hansen MR, Hansen CL, Madsen D, Tanner D, Nielsen TE. Chem. Eur. J. 2014; 20: 3297
35d Zhao C, Chen SB, Seidel D. J. Am. Chem. Soc. 2016; 138: 9053

36 Chen J, Han X, Lu X. Angew. Chem. Int. Ed. 2017; 56: 14698

For excellent reviews on the Heck reaction, see:

37a Heck RF. Acc. Chem. Res. 1979; 12: 146
37b Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
37c Negishi E, Copéret C, Ma S, Liou S.-Y, Liu F. Chem. Rev. 1996; 96: 3650

38a Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
38b Negishi E. Angew. Chem. Int. Ed. 2011; 50: 6738
38c Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722

39 Wang G, Li J.-C, Zhou Y.-G, Ye Z.-S. Org. Lett. 2021; 23: 802
40 He Y.-P, Cao J, Wu H, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2021; 60: 7093
41 Cao J, Wu H, Wang Q, Zhu J. Nat. Chem. 2021; 13: 671
42 Yuan K, Liu L, Chen J, Guo S, Yao H, Lin A. Org. Lett. 2018; 20: 3477
43 Whyte A, Bajohr J, Arora R, Torelli A, Lautens M. Angew. Chem. Int. Ed. 2021; 60: 20231

44a Littell R, Greenblatt EN, Allen GR. J. Med. Chem. 1972; 15: 875
44b Kam TS, Subramaniam G, Chen W. Phytochemistry 1999; 51: 159
44c Zeng T, Wu X.-Y, Yang S.-X, Lai W.-C, Shi S.-D, Zou Q, Liu Y, Li L.-M. J. Nat. Prod. 2017; 80: 864
44d Yap W.-S, Gan C.-Y, Sim K.-S, Lim S.-H, Low Y.-Y, Kam T.-S. J. Nat. Prod. 2016; 79: 230
44e Li Y, Li J, Ding H, Li A. Natl. Sci. Rev. 2017; 4: 397
44f Li L, Chen Z, Zhang X, Jia Y. Chem. Rev. 2018; 118: 3752
44g Usman M, Hu X.-D, Liu W.-B. Chin. J. Chem. 2020; 38: 737
44h Wang N, Jiang X. Chem. Rec. 2021; 21: 295

45 Hu X.-D, Chen Z.-H, Zhao J, Sun R.-Z, Zhang H, Qi X, Liu W.-B. J. Am. Chem. Soc. 2021; 143: 3734

46a Tietze LF. Chem. Rev. 1996; 96: 115
46b Lee JM, Na Y, Han H, Chang S. Chem. Soc. Rev. 2004; 33: 302
46c Wasilke JC, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
46d Ambrosini LM, Lambert TH. ChemCatChem 2010; 2: 1373
46e Ramachary DB, Jain S. Org. Biomol. Chem. 2011; 9: 1277
46f Lohr TL, Marks TJ. Nat. Chem. 2015; 7: 477
46g Wang P.-S, Chen D.-F, Gong L.-Z. Top. Curr. Chem. 2020; 378: 9
46h Wang P.-S, Li K.-N, Zhou X.-L, Wu X, Han Z.-Y, Guo R, Gong L.-Z. Chem. Eur. J. 2013; 19: 6234

47 Zhao F, Li N, Zhu Y.-F, Han Z.-Y. Org. Lett. 2016; 18: 1506
48 Yang G, Pan J, Ke Y.-M, Liu Y, Zhao Y. Angew. Chem. Int. Ed. 2021; 60: 20689