Recent Progress towards the Transition-Metal-Catalyzed Dearomatizing Spirocyclization Reactions of Indolyl Ynones

Kua-Fei Wei; Xiao-Lei Jiang; Guang-Xin Ru; Xiu-Hong Zhu; Wen-Bo Shen

doi:10.1055/a-1970-4290

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(03): 211-220
DOI: 10.1055/a-1970-4290

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Recent Progress towards the Transition-Metal-Catalyzed Dearomatizing Spirocyclization Reactions of Indolyl Ynones

Autor*innen

Kua-Fei Wei

^aCollege of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
Xiao-Lei Jiang

^aCollege of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China

^bSanmenxia Polytechnic, Sanmenxia, Henan 472000, P. R. of China
Guang-Xin Ru

^aCollege of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
Xiu-Hong Zhu

^aCollege of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
Wen-Bo Shen∗

^aCollege of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

Dearomatizing spirocyclization reactions are very appealing synthetic strategies to generate functionalized three-dimensional scaffolds from simple two-dimensional precursors. Recently, the field of transition-metal-catalyzed dearomatizing spirocyclization reactions of indolyl ynones has burgeoned, as the construction of synthetically challenging quaternary spirocyclic carbons is easily achieved. In this review, we introduce an overview of advances in the transition-metal-catalyzed dearomatizing spirocyclization reactions of indolyl ynones, with the reactions being categorized according to type of catalyst.

Key words

transition-metal catalysis - indolyl ynones - dearomatization - spirocyclization - spirocyclic indolenines

Volltext

Referenzen

References and Notes

For selected examples, see:

1a Liu C.-T, Wang Q.-W, Wang C.-H. J. Am. Chem. Soc. 1981; 103: 4634
1b Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540
1c Jadulco R, Edrada RA, Ebel R, Berg A, Schaumann K, Wray V, Steube K, Proksch P. J. Nat. Prod. 2004; 67: 78
1d Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
1e Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673
1f Zhou X.-J, Liu H.-Y, Mo Z.-Y, Ma X.-L, Chen Y.-Y, Tang H.-T, Pan Y.-M, Xu Y.-L. Chem. Asian J. 2020; 15: 1536

2a Zheng C, You S.-L. Acc. Chem. Res. 2020; 53: 974
2b Varlet T, Matišić M, Elslande EV, Neuville L, Gandon V, Masson G. J. Am. Chem. Soc. 2021; 143: 11611
2c Nie Y.-H, Komatsuda M, Yang P, Zheng C, Yamaguchi J, You S.-L. Org. Lett. 2022; 24: 1481
2d Becker A, Grugel CP, Breit B. Org. Lett. 2021; 23: 3788
2e Sabat N, Soualmia F, Retailleau P, Benjdia A, Berteau O, Guinchard X. Org. Lett. 2020; 22: 4344
2f Wu Q.-F, He H, Liu W.-B, You S.-L. J. Am. Chem. Soc. 2010; 132: 11418
2g Zhang Y.-Q, Chen Y.-B, Liu J.-R, Wu S.-Q, Fan X.-Y, Zhang Z.-X, Hong X, Ye L.-W. Nat. Chem. 2021; 13: 1093

3a Zhang B, Li X, Ai Z, Zhao B, Yu Z, Du Y. Org. Lett. 2022; 24: 390
3b Ho HE, Pagano A, Rossi-Ashton JA, Donald JR, Epton RG, Churchill JC, James MJ, O’Brien P, Taylor RJ. K, Unsworth WP. Chem. Sci. 2020; 11: 1353

For selected reviews, see:

4a Zhuo C.-X, Zheng C, You S.-L. Acc. Chem. Res. 2014; 47: 2558
4b Liebov BK, Harman WD. Chem. Rev. 2017; 117: 13721
4c Remy R, Bochet CG. Chem. Rev. 2016; 116: 9816
4d Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
4e Ortiz FL, Iglesias MJ, Fernández I, Sánchez CM. A, Gómez GR. Chem. Rev. 2007; 107: 1580
4f Pape AR, Kaliappan KP, Kündig EP. Chem. Rev. 2000; 100: 2917

For selected reviews, see:

5a Zheng C, You S.-L. Acc. Chem. Res. 2020; 53: 974
5b Zheng C, You S.-L. ACS Cent. Sci. 2021; 7: 432
5c Saya JM, Ruijter E, Orru RV. A. Chem. Eur. J. 2019; 25: 8916
5d Roche SP, Tendoung J.-JY. Tréguier B. Tetrahedron 2015; 71: 3549

For selected reviews, see:

6a Zheng Z, Ma X, Cheng X, Zhao K, Gutman K, Li T, Zhang L. Chem. Rev. 2021; 121: 8979
6b Zhang L. Acc. Chem. Res. 2014; 47: 877
6c Yeom H.-S, Shin S. Acc. Chem. Res. 2014; 47: 966
6d Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
6e Qian D, Zhang J. Chem. Soc. Rev. 2015; 44: 677
6f Ye L.-W, Zhu X.-Q, Sahani RL, Xu Y, Qian P.-C, Liu R.-S. Chem. Rev. 2021; 121: 9039
6g Shen W.-B, Tang X.-T. Org. Biomol. Chem. 2019; 17: 7106
6h Ru G.-X, Zhang T.-T, Zhang M, Jiang X.-L, Wan Z.-K, Zhu X.-H, Shen W.-B, Gao G.-Q. Org. Biomol. Chem. 2021; 19: 5274
6i Gao G.-Q, Ma G, Jiang X.-L, Liu Q, Fan C.-L, Lv D.-C, Su H, Ru G.-X, Shen W.-B. Org. Biomol. Chem. 2022; 20: 5035
6j Tang X.-T, Yang F, Zhang T.-T, Liu Y.-F, Liu S.-Y, Su T.-F, Lv D.-C, Shen W.-B. Catalysts 2020; 10: 350

7a Fedoseev P, Coppola G, Ojeda GM, Eycken EV. V. Chem. Commun. 2018; 54: 3625
7b Fedoseev P, Eycken EV. Chem. Commun. 2017; 53: 7732
7c Han G, Xue L, Zhao L, Zhu T, Hou J, Song Y, Liu Y. Adv. Synth. Catal. 2019; 361: 678

For selected examples, see:

8a Shen W.-B, Tang X.-T, Zhang T.-T, Lv D.-C, Zhao D, Su T.-F, Meng L. Org. Lett. 2021; 23: 1285
8b Shen W.-B, Zhang T.-T, Zhang M, Wu J.-J, Jiang X.-L, Ru G.-X, Gao G.-Q, Zhu X.-H. Org. Chem. Front. 2021; 8: 4960
8c Shen W.-B, Tang X.-T, Zhang T.-T, Liu S.-Y, He J.-M, Su T.-F. Org. Lett. 2020; 22: 6799
8d Zheng Y, Zhang T.-T, Shen W.-B. Org. Biomol. Chem. 2021; 19: 9688
8e Zhang T.-T, Wei K.-F, Ru G.-X, Zhu X.-H, Xie L.-X, Shen W.-B. Synlett 2022; in press

9 James MJ, Cuthbertson JD, O’Brien P, Taylor RJ. K, Unsworth WP. Angew. Chem. Int. Ed. 2015; 54: 7640
10 Clarke AK, James MJ, O’Brien P, Taylor RJ. K, Unsworth WP. Angew. Chem. Int. Ed. 2016; 55: 13798

For Ag-NPs in catalysis, see:

11a Bhosale MA, Bhanage BM. Curr. Org. Chem. 2015; 19: 708
11b Cong H, Porco JA. ACS Catal. 2012; 2: 65
11c Shimizu K.-I, Sato R, Satsuma A. Angew. Chem. Int. Ed. 2009; 48: 3982
11d Mitsudome T, Arita S, Mori H, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2008; 47: 7938
11e Qi C, Qin T, Suzuki D, Porco JA. J. Am. Chem. Soc. 2014; 136: 3374

12 Liddon JT. R, Clarke AK, Taylor RJ. K, Unsworth WP. Org. Lett. 2016; 18: 6328
13 Liddon JT. R, Rossi-Ashton JA, Clarke AK, Lynam JM, Taylor RJ. K, Unsworth WP. Synthesis 2018; 50: 4829
14 Ho HE, Stephens TC, Payne TJ, O’Brien P, Taylor RJ. K, Unsworth WP. ACS Catal. 2019; 9: 504

For prominent examples of the use of Pd-catalysis in dearomatizing spirocyclization, see:

15a Kimura M, Futamata M, Mukai R, Tamaru Y. J. Am. Chem. Soc. 2005; 127: 4592
15b Rousseaux S, García-Fortanet J, Del Aguila Sanchez MA, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 9282
15c Wu K.-J, Dai LX, You S.-L. Org. Lett. 2012; 14: 3772
15d Montgomery TD, Nibbs AE, Zhu Y, Rawal VH. Org. Lett. 2014; 16: 3480
15e Gao S, Wu Z, Fang X, Lin A, Yao H. Org. Lett. 2016; 18: 3906
15f Hu W, Wang H, Bai L, Liu J, Luan X. Org. Lett. 2018; 20: 880

16 Liddon JT. R, James MJ, Clarke AK, O’Brien P, Taylor RJ. K, Unsworth WP. Chem. Eur. J. 2016; 22: 8777
17 Li C, Xue L, Zhou J, Zhao Y, Han G, Hou J, Song Y, Liu Y. Org. Lett. 2020; 22: 3291

18a Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
18b Meanwell NA. J. Med. Chem. 2018; 61: 5822
18c Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA. J. Med. Chem. 2015; 58: 8315
18d Wang J, Sánchez-Roselló M, Aceña JL, Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432

19 Inprung N, Ho HE, Rossi-Ashton JA, Epton RG, Whitwood AC, Lynam JM, Taylor RJ. K, James MJ, Unsworth WP. Org. Lett. 2022; 24: 668
20 Ru G.-X, Zhang M, Zhang T.-T, Jiang X.-L, Gao G.-Q, Zhu X.-H, Wang S, Fan C.-L, Li X, Shen W.-B. Org. Chem. Front. 2022; 9: 2621