Asymmetric Brønsted Acid Catalyzed Cycloadditions of ortho-Quinone Methides and Related Compounds

Caroline Dorsch; Christoph Schneider

doi:10.1055/a-1781-6538

Synthesis, Table of Contents

Synthesis 2022; 54(14): 3125-3141
DOI: 10.1055/a-1781-6538

review

Asymmetric Brønsted Acid Catalyzed Cycloadditions of ortho-Quinone Methides and Related Compounds

Caroline Dorsch

,

Christoph Schneider ∗

Abstract

All articles of this category

Dedicated to Prof. Dr. Lutz F. Tietze with deep respect and admiration on the occasion of his 80^th birthday

Abstract

This review summarizes recent developments in the area of Brønsted acid catalyzed, enantioselective cycloadditions of ortho-quinone methides, ortho-quinone methide imines as well as heterocyclic indole- and pyrrole-based methides. In a straightforward and single-step transformation complex polycyclic N- and O-heterocyclic scaffolds are accessible, with typically good yields and excellent stereocontrol, from simple benzyl and heterobenzyl alcohols upon acid-catalyzed dehydration. The transient precursors are hydrogen-bonded to a chiral Brønsted acid which controls the enantioselectivity of the process.

1 Introduction

2 Cycloadditions of ortho-Quinone Methides

2.1 Brønsted Acid Catalyzed Processes

2.2 Cooperative Brønsted Acid/Transition-Metal-Catalyzed Processes

3 Cycloadditions of ortho-Quinone Methide Imines

4 Cycloadditions of Indolyl-3-methides

5 Cycloadditions of Indolyl-2-methides

5.1 Brønsted Acid Catalyzed Processes

5.2 Cooperative Brønsted Acid/Transition-Metal-Catalyzed Processes

6 Cycloadditions of Pyrrolyl-2-methides

7 Cycloadditions of Pyrrolyl-3-methides

8 Conclusions

Key words

cycloaddition - heterocycles - indoles - pyrroles - chromans - enantioselectivity - Brønsted acid catalysis

Full Text

References

References

1a van de Water RW, Pettus TR. R. Tetrahedron 2002; 58: 5367
1b Pathak TP, Sigman MS. J. Org. Chem. 2011; 76: 9210
1c Bai W.-J, David JG, Feng Z.-G, Weaver MG, Wu K.-L, Pettus TR. R. Acc. Chem. Res. 2014; 47: 3655
1d Wang Z, Sun J. Synthesis 2015; 47: 3629
1e Caruana L, Fochi M, Bernardi L. Molecules 2015; 20: 11733
1f Jaworski AA, Scheidt KA. J. Org. Chem. 2016; 81: 10145
1g Nielsen CD.-T, Abas H, Spivey AC. Synthesis 2018; 50: 4008
1h Yang B, Gao S. Chem. Soc. Rev. 2018; 47: 7926

2 Wilcke D, Herdtweck E, Bach T. Synlett 2011; 1235

3a El-Sepelgy O, Haseloff S, Alamsetti SK, Schneider C. Angew. Chem. Int. Ed. 2014; 53: 7923
3b Göricke F, Haseloff S, Laue M, Schneider M, Brumme T, Schneider C. J. Org. Chem. 2020; 85: 11699

4a Saha S, Schneider C. Chem. Eur. J. 2015; 21: 2348
4b Saha S, Schneider C. Org. Lett. 2015; 17: 648

5 Hsiao CC, Raja S, Liao HH, Atodiresei I, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 5762

6a Zhao JJ, Sun SB, He SH, Wu Q, Shi F. Angew. Chem. Int. Ed. 2015; 54: 5460
6b Tu M.-S, Liu S.-J, Zhong C, Zhang S, Zhang H, Zheng Y.-L, Shi F. J. Org. Chem. 2020; 85: 5403

7 Liu S.-J, Tu M.-S, Liu K.-Y, Chen J.-Y, Ni S.-F, Zhang Y.-C, Shi F. Molecules 2021; 26: 6751
8 Zhang H, Liu G, Guan X, Gao J, Qin X, Jiang G, Sun D, Zhang G, Zhang S. Eur. J. Org. Chem. 2019; 7264
9 You Y, Li T.-T, Yuan S.-P, Xie K.-X, Wang Z.-H, Zhao J.-Q, Zhou M.-Q, Yuan W.-C. Chem. Commun. 2020; 56: 439
10 Feng S, Yang B, Chen T, Wang R, Deng YH, Shao Z. J. Org. Chem. 2020; 85: 5231
11 Wang Z, Sun J. Org. Lett. 2017; 19: 2934
12 Jeong HJ, Kim DY. Org. Lett. 2018; 20: 2944
13 Spanka M, Schneider C. Org. Lett. 2018; 20: 4769
14 Gheewala CD, Hirschi JS, Lee WH, Paley DW, Vetticatt MJ, Lambert TH. J. Am. Chem. Soc. 2018; 140: 3523
15 Gheewala CD, Collins BE, Lambert TH. Science 2016; 351: 961
16 Xie Y, List B. Angew. Chem. Int. Ed. 2017; 56: 4936
17 Nielsen CD. T, Mooji WJ, Sale D, Rzepa HS, Bures J, Spivey AC. Chem. Sci. 2019; 10: 406
18 Zhu Z, Odagi M, Supantanapong N, Xu W, Saame J, Kirm HU, Abboud KA, Leito I, Seidel D. J. Am. Chem. Soc. 2020; 142: 15252
19 Klausen RS, Jacobsen EN. Org. Lett. 2009; 11: 887
20 Sun M, Ma C, Zhou S.-J, Lou S.-F, Xiao J, Jiao Y, Shi F. Angew. Chem. Int. Ed. 2019; 58: 8703
21 Suneja A, Schneider C. Org. Lett. 2018; 20: 7576
22 Pandit RP, Kim ST, Ryu DH. Angew. Chem. Int. Ed. 2019; 58: 13427

Selected reviews:

23a Wang MH, Scheidt KA. Angew. Chem. Int. Ed. 2016; 55: 14912
23b Afewerki F, Córdova A. Chem. Rev. 2016; 116: 13512
23c Deng Y, Kumar S, Wang H. Chem. Commun. 2014; 50: 4272
23d Pellissier H. Tetrahedron 2013; 69: 7171
23e Guo X, Hu W. Acc. Chem. Res. 2013; 46: 2427
23f Du Z, Shao Z. Chem. Soc. Rev. 2013; 42: 1337
23g Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
23h Wende RP, Schreiner PR. Green Chem. 2012; 14: 1821

24 Alamsetti SK, Spanka M, Schneider C. Angew. Chem. Int. Ed. 2016; 55: 2392
25 Suneja A, Loui HJ, Schneider C. Angew. Chem. Int. Ed. 2020; 59: 5536
26 Göricke F, Schneider C. Angew. Chem. Int. Ed. 2018; 57: 14736

Selected reviews:

27a Sodeoka M, Hamashima Y. Pure Appl. Chem. 2006; 78: 477
27b Hamashima Y, Sodeoka M. Synlett 2006; 1467
27c Sodeoka M, Hamashima Y. Pure Appl. Chem. 2008; 80: 763
27d Sodeoka M, Hamashima Y. Chem. Commun. 2009; 5787

28 Liao H.-H, Chatupheeraphat A, Hsiao C.-C, Atodiresei I, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 15540
29 Chatupheeraphat A, Liao H.-H, Mader S, Sako M, Sasai H, Atodiresei I, Rueping M. Angew. Chem. Int. Ed. 2016; 55: 4803
30 Kretzschmar M, Hodik T, Schneider C. Angew. Chem. Int. Ed. 2016; 55: 9788
31 Hodik T, Schneider C. Org. Biomol. Chem. 2017; 15: 3706
32 Hodik T, Schneider C. Chem. Eur. J. 2018; 24: 18082
33 Liao H.-H, Hisao C.-C, Atodiresei I, Rueping M. Chem. Eur. J. 2018; 24: 7718
34 Li L.-Z, Wang C.-S, Guo W.-F, Mei G.-J, Shi F. J. Org. Chem. 2018; 83: 614
35 Kretzschmar M, Hofmann F, Moock D, Schneider C. Angew. Chem. Int. Ed. 2018; 57: 4774
36 Hofmann F, Gärtner C, Kretzschmar M, Schneider C. Synthesis 2022; 54: 1055

Selected reviews:

37a Kataja AO, Masson G. Tetrahedron 2014; 70: 8783
37b Wang L, Chen Y, Xiao J. Asian J. Org. Chem. 2014; 3: 1036
37c Wu H, Ye YP, Shi F. Synthesis 2015; 47: 1990
37d Mei GJ, Shi F. J. Org. Chem. 2017; 82: 7695
37e Zhang YC, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425

38 Tan W, Li X, Gong Y.-X, Ge M.-D, Shi F. Chem. Commun. 2014; 50: 15901
39 Shi F, Zhang H.-H, Sun X.-X, Liang J, Fan T, Tu S.-J. Chem. Eur. J. 2015; 21: 3465

40a Dai W, Lu H, Li X, Shi F, Tu S.-J. Chem. Eur. J. 2014; 20: 11382
40b Shi F, Zhu R.-Y, Dai W, Wang C.-S, Tu S.-J. Chem. Eur. J. 2014; 20: 2597

41 Lebee C, Kataja AO, Blanchard F, Masson G. Chem. Eur. J. 2015; 21: 8399
42 Gelis C, Levitre G, Merad J, Retailleau P, Neuville L, Masson G. Angew. Chem. Int. Ed. 2018; 57: 12121
43 Varlet T, Matisic M, Van Elsande E, Neuville L, Gandon V, Masson G. J. Am. Chem. Soc. 2021; 143: 11611

44a Qi S, Liu CY, Ding JY, Han FS. Chem. Commun. 2014; 50: 8605
44b Liu CY, Han FS. Chem. Commun. 2015; 51: 11844

45 Bera K, Schneider C. Chem. Eur. J. 2016; 22: 7074
46 Bera K, Schneider C. Org. Lett. 2016; 18: 5660
47 Zhu Z.-Q, Yin L, Wang Y, Shen Y, Li C, Mei G.-J, Shi F. Org. Chem. Front. 2017; 4: 57
48 Sun X.-X, Li C, He Y.-Y, Zhu Z.-Q, Mei G.-J, Shi F. Adv. Synth. Catal. 2017; 359: 2660
49 Galvan A, Gonzalez-Perez AB, Alvarez R, de Lera AR, Fananas FJ, Rodriguez F. Angew. Chem. Int. Ed. 2016; 55: 3428
50 Zhu ZQ, Shen Y, Sun XX, Tao JY, Liu JX, Shi F. Adv. Synth. Catal. 2016; 358: 3797
51 Xu M.-M, Wang H.-Q, Wan Y, Wang S.-L, Shi F. J. Org. Chem. 2017; 82: 10226
52 Sun XX, Zhang HH, Li GH, He YY, Shi F. Chem. Eur. J. 2016; 22: 17526
53 Li T.-Z, Liu S.-J, Sun Y.-W, Deng S, Tan W, Jiao Y, Zhang Y.-W, Shi F. Angew. Chem. Int. Ed. 2021; 60: 2355
54 Wang C.-S, Wu J.-L, Li C, Li L.-Z, Mei G.-J, Shi F. Adv. Synth. Catal. 2018; 360: 846
55 Wu J.-L, Wang J.-Y, Wu P, Wang J.-R, Mei G.-J, Shi F. Org. Chem. Front. 2018; 5: 1436
56 Göricke F, Schneider C. Org. Lett. 2020; 22: 6101
57 Loui HJ, Suneja A, Schneider C. Org. Lett. 2021; 23: 2578
58 Torssell KB. G. Natural Product Chemistry: A Mechanistic, Biosynthetic and Ecological Approach, 2nd ed. Apotekarsocieteten, Swedish Pharmaceutical Society; Stockholm: 1997
59 Brown DS, Earle MJ, El Gihani MT, Heaney H. Synlett 1995; 269
60 Kallweit I, Schneider C. Org. Lett. 2019; 21: 519
61 Zyrus, J.; Kallweit, I.; Schneider, C. unpublished results.
62 Kallweit I, Laue M, Schneider C. Org. Lett. 2020; 22: 9065
63 Sarkar, R.; Kallweit, I.; Schneider, C. unpublished results.