Lewis Acid Catalyzed Cycloaddition Reaction of Bicyclo[1.1.0]butanes

Hui Yang; Jie Chen; Ling Zhou

doi:10.1055/a-2456-9789

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2456-9789

synpacts

Lewis Acid Catalyzed Cycloaddition Reaction of Bicyclo[1.1.0]butanes

Hui Yang

^bCollege of Chemistry and Chemical Engineering, Xi’an University of Science and Technology, Xi’an, 710054, P. R. of China

,

Jie Chen∗

^aKey Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an, 710127, P. R. of China

,

Ling Zhou∗

^aKey Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an, 710127, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

In recent years, formal cycloaddition reactions involving bicyclo[1.1.0]butanes (BCBs) have furnished an array of innovative methodologies and strategies for the efficient synthesis of bicyclo[2.1.1]hexanes (BCHs). Most methods can be broadly classified into two main modes: the radical pathway and the two-electron pathway. This Synpacts article will summarize the recent advancements in Lewis acid catalyzed formal cycloaddition reactions involving BCBs with alkenes, dipolar molecules, and alkynes, spanning the period from 2022 to 2024. Additionally, we introduce the formal cycloaddition reaction of BCBs with ynamides, catalyzed by Sc(OTf)₃, which has been recently developed by our group. This approach offers a novel and efficient method for the synthesis of polysubstituted 2-amino-bicyclo[2.1.1]hexenes.

1 Introduction

2 Lewis Acid Catalyzed Formal Cycloaddition of BCBs with Alkenes and Dipoles

3 Lewis Acid Catalyzed Formal Cycloaddition of BCBs with Alkynes

4 Conclusion

Key words

alkynes - bicyclic compounds - cyclization - cycloaddition - Lewis acids

Full Text

References

References
1 Baeyer A. Ber. Dtsch. Chem. Ges. 1885; 18: 2269

For selected reviews, see:

2a Walczak MA. A, Krainz T, Wipf P. Acc. Chem. Res. 2015; 48: 1149
2b Fawcett A. Pure Appl. Chem. 2020; 92: 751
2c Turkowska J, Durka J, Gryko D. Chem. Commun. 2020; 56: 5718
2d Kelly CB, Milligan JA, Tilley LJ, Sodano TM. Chem. Sci. 2022; 13: 11721
2e Bellotti P, Glorius F. J. Am. Chem. Soc. 2023; 145: 20716
2f Golfmann M, Walker JC. L. Commun. Chem. 2023; 6: 9
2g Hu Q.-Q, Chen J, Yang Y, Yang H, Zhou L. Tetrahedron Chem. 2024; 9: 100070
2h Sujansky SJ, Ma X. Asian J. Org. Chem. 2024; 13: e202400045

3a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
3b Meanwell NA. J. Med. Chem. 2011; 54: 2529
3c Das P, Delost MD, Qureshi MH, Smith DT, Njardarson JT. J. Med. Chem. 2019; 62: 4265
3d Mykhailiuk PK. Org. Biomol. Chem. 2019; 17: 2839
3e Denisenko A, Garbuz P, Shishkina SV, Voloshchuk NM, Mykhailiuk PK. Angew. Chem. Int. Ed. 2020; 59: 20515
3f Levterov VV, Panasyuk Y, Pivnytska VO, Mykhailiuk PK. Angew. Chem. Int. Ed. 2020; 59: 7161
3g Subbaiah MA. M, Meanwell NA. J. Med. Chem. 2021; 64: 14046
3h Tsien J, Hu C, Merchant RR, Qin T. Nat. Rev. Chem. 2024; 8: 605

4a Kleinnijenhuis RA, Timmer BJ. J, Lutteke G, Smits JM. M, de Gelder R, van Maarseveen JH, Hiemstra H. Chem. Eur. J. 2016; 22: 1266
4b Takao K.-i, Kai H, Yamada A, Fukushima Y, Komatsu D, Ogura A, Yoshida K. Angew. Chem. Int. Ed. 2019; 58: 9851
4c Herter L, Koutsopetras I, Turelli L, Fessard T, Salomé C. Org. Biomol. Chem. 2022; 20: 9108
4d Rigotti T, Bach T. Org. Lett. 2022; 24: 8821
4e Denisenko A, Garbuz P, Makovetska Y, Shablykin O, Lesyk D, Al-Maali G, Korzh R, Sadkova IV, Mykhailiuk PK. Chem. Sci. 2023; 14: 14092
4f Denisenko A, Garbuz P, Voloshchuk NM, Holota Y, Al-Maali G, Borysko P, Mykhailiuk PK. Nat. Chem. 2023; 15: 1155
4g Paul S, Adelfinsky D, Salome C, Fessard T, Brown MK. Chem. Sci. 2023; 14: 8070
4h Reinhold M, Steinebach J, Golz C, Walker JC. L. Chem. Sci. 2023; 14: 9885
4i Posz JM, Sharma N, Royalty PA, Liu Y, Salome C, Fessard TC, Brown MK. J. Am. Chem. Soc. 2024; 146: 10142

5 Wipf P, Walczak MA. A. Angew. Chem. Int. Ed. 2006; 45: 4172

6a Cairncross A, Blanchard EP. Jr. J. Am. Chem. Soc. 1966; 88: 496
6b Meijere AD, Wenck H, Seyed-Mahdavi F, Viehe HG, Gallez V, Erden I. Tetrahedron 1986; 42: 1291

7a Guo R, Chang Y.-C, Herter L, Salome C, Braley SE, Fessard TC, Brown MK. J. Am. Chem. Soc. 2022; 144: 7988
7b Kleinmans R, Pinkert T, Dutta S, Paulisch TO, Keum H, Daniliuc CG, Glorius F. Nature 2022; 605: 477
7c Liang Y, Kleinmans R, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2022; 144: 20207
7d Xu M, Wang Z, Sun Z, Ouyang Y, Ding Z, Yu T, Xu L, Li P. Angew. Chem. Int. Ed. 2022; 61: e202214507
7e Agasti S, Beltran F, Pye E, Kaltsoyannis N, Crisenza GE. M, Procter DJ. Nat. Chem. 2023; 15: 535
7f de Robichon M, Kratz T, Beyer F, Zuber J, Merten C, Bach T. J. Am. Chem. Soc. 2023; 145: 24466
7g Kleinmans R, Dutta S, Ozols K, Shao H, Schäfer F, Thielemann RE, Chan HT, Daniliuc CG, Houk KN, Glorius F. J. Am. Chem. Soc. 2023; 145: 12324
7h Liu Y, Lin S, Li Y, Xue J.-H, Li Q, Wang H. ACS Catal. 2023; 13: 5096
7i Nguyen TV. T, Bossonnet A, Wodrich MD, Waser J. J. Am. Chem. Soc. 2023; 145: 25411
7j Yan H, Liu Y, Feng X, Shi L. Org. Lett. 2023; 25: 8116
7k Dutta S, Lee D, Ozols K, Daniliuc CG, Shintani R, Glorius F. J. Am. Chem. Soc. 2024; 146: 2789
7l Dutta S, Lu Y.-L, Erchinger JE, Shao H, Studer E, Schäfer F, Wang H, Rana D, Daniliuc CG, Houk KN, Glorius F. J. Am. Chem. Soc. 2024; 146: 5232
7m Fu Q, Cao S, Wang J, Lv X, Wang H, Zhao X, Jiang Z. J. Am. Chem. Soc. 2024; 146: 8372
7n Ren H, Li T, Xing J, Li Z, Zhang Y, Yu X, Zheng J. Org. Lett. 2024; 26: 1745
7o Tyler JL, Schäfer F, Shao H, Stein C, Wong A, Daniliuc CG, Houk KN, Glorius F. J. Am. Chem. Soc. 2024; 146: 16237

8 Dhake K, Woelk KJ, Becica J, Un A, Jenny SE, Leitch DC. Angew. Chem. Int. Ed. 2022; 61: e202204719
9 Radhoff N, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2023; 62: e202304771
10 Liang Y, Paulus F, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2023; 62: e202305043

11a Huck CJ, Sarlah D. Chem 2020; 6: 1589
11b Cheng Y.-Z, Feng Z, Zhang X, You S.-L. Chem. Soc. Rev. 2022; 51: 2145

12 Ni D, Hu S, Tan X, Yu Y, Li Z, Deng L. Angew. Chem. Int. Ed. 2023; 62: e202308606
13 Tang L, Xiao Y, Wu F, Zhou J.-L, Xu T.-T, Feng J.-J. Angew. Chem. Int. Ed. 2023; 62: e202310066
14 Zhang K, Tian S, Li W, Yang X, Duan X.-H, Guo L.-N, Li P. Org. Lett. 2024; 26: 5482
15 Wang J.-J, Tang L, Xiao Y, Wu W.-B, Wang G, Feng J.-J. Angew. Chem. Int. Ed. 2024; 63: e202405222
16 Su J.-Y, Zhang J, Xin Z.-Y, Li H, Zheng H, Deng W.-P. Org. Chem. Front. 2024; 11: 4539
17 Nicolai S, Waser J. Chem. Sci. 2024; 15: 10823
18 Zhang J, Su J.-Y, Zheng H, Li H, Deng W.-P. Angew. Chem. Int. Ed. 2024; 63: e202318476
19 Liang Y, Nematswerani R, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2024; 63: e202402730
20 Hu S, Pan Y, Ni D, Deng L. Nat. Commun. 2024; 15: 6128
21 Zhu S, Tian X, Li S.-W. Org. Lett. 2024; 26: 6309
22 Lin Z, Ren H, Lin X, Yu X, Zheng J. J. Am. Chem. Soc. 2024; 146: 18565
23 Yang L, Wang H, Lang M, Wang J, Peng S. Org. Lett. 2024; 26: 4104
24 Wang X, Gao R, Li X. J. Am. Chem. Soc. 2024; 146: 21069
25 Wu F, Wu W.-B, Xiao Y, Li Z, Tang L, He H.-X, Yang X.-C, Wang J.-J, Cai Y, Xu T.-T, Tao J.-H, Wang G, Feng J.-J. Angew. Chem. Int. Ed. 2024; 63: e202406548

26a Yang H, Sun H.-R, He R.-Q, Yu L, Hu W, Chen J, Yang S, Zhang G.-G, Zhou L. Nat. Commun. 2022; 13: 632
26b Gou B.-B, Tang Y, Lin Y.-H, Yu L, Jian Q.-S, Sun H.-R, Chen J, Zhou L. Angew. Chem. Int. Ed. 2022; 61: e202208174
26c Sun H.-R, Yang L, Li Y, Yu L, Gou B.-B, Sharif A, Jian Q.-S, Chen J, Zhou L. Sci. China Chem. 2023; 66: 2292
26d Wang L.-Y, Yang L, Chen J, Zhou L. Synlett 2023; 34: 1200

27 Sodano TM, Combee LA, Stephenson CR. J. ACS Med. Chem. Lett. 2020; 11: 1785
28 Hu Q.-Q, Wang L.-Y, Chen X.-H, Geng Z.-X, Chen J, Zhou L. Angew. Chem. Int. Ed. 2024; 63: e202405781

29a Mackay WD, Fistikci M, Carris RM, Johnson JS. Org. Lett. 2014; 16: 1626
29b Liu D, Guo X, Zhou S, Guo L, Zhang X. J. Org. Chem. 2024; 89: 1241
29c McNamee RE, Frank N, Christensen KE, Duarte F, Anderson EA. Sci. Adv. 2024; 10: eadj9695

30 While this manuscript was under preparation, Biju and co-workers reported a similar Sc(OTf)₃-catalyzed cycloaddition of BCBs with ynamides, see: Sarkar D, Deswal S, Das RC, Biju AT. Chem. Sci. 2024; 15: 16243