Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

Regina Westphal; Eclair Venturini Filho; Fabrizio Medici; Maurizio Benaglia; Sandro J. Greco

doi:10.1055/a-1771-0641

Synthesis, Table of Contents

Synthesis 2022; 54(13): 2927-2975
DOI: 10.1055/a-1771-0641

review

Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

Regina Westphal

^aChemistry Department, Espírito Santo Federal University, Avenida Fernando Ferrari 514, Goiabeiras, Vitória, ES, Brazil

,

Eclair Venturini Filho

^aChemistry Department, Espírito Santo Federal University, Avenida Fernando Ferrari 514, Goiabeiras, Vitória, ES, Brazil

,

Fabrizio Medici

^bDipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19 Milano, Italy

,

Maurizio Benaglia ∗

^bDipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19 Milano, Italy

,

Sandro J. Greco∗

^aChemistry Department, Espírito Santo Federal University, Avenida Fernando Ferrari 514, Goiabeiras, Vitória, ES, Brazil

› Author Affiliations

Abstract

All articles of this category

Abstract

This review summarizes the latest developments in asymmetric domino reactions, with the emphasis on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, the reaction mechanisms, the rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included when appropriate.

1 Introduction

2 Asymmetric Domino Reactions

2.1 Domino Reactions Initiated by Michael Reactions

2.2 Domino Reactions Initiated by Mannich Reactions

2.3 Domino Reactions Initiated by Knoevenagel Reactions

2.4 Domino Reactions Initiated by Cycloaddition Reactions

2.5 Domino Reactions Initiated by Metal Insertion

2.6 Other Mechanisms

3 Conclusion

Key words

domino reactions - spiro compounds - stereoselective synthesis - organocatalysis - natural products

Full Text

References

References
1 Rios R. Chem. Soc. Rev. 2012; 41: 1060

2a Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673
2b Saraswat P, Jeyabalan G, Hassan MZ, Rahman MU, Nyola NK. Synth. Commun. 2016; 46: 1643
2c Zheng Y.-J, Tice CM. Expert Opin. Drug Discovery 2016; 11: 831

3 Ding A, Meazza M, Guo H, Yang JW, Rios R. Chem. Soc. Rev. 2018; 47: 5946
4 Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2003: 2209
5 Sansinenea E, Martínez EF, Ortiz A. Eur. J. Org. Chem. 2020; 2020: 5101
6 Saragi TP. I, Spehr T, Siebert A, Fuhrmann-Lieker T, Salbeck J. Chem. Rev. 2007; 107: 1011

7a Pfau A, Plattner P. Helv. Chim. Acta 1939; 22: 640
7b Chupakhin E, Babich O, Prosekov A, Asyakina L, Krasavin M. Molecules 2019; 24: 4165
7c Smith LK, Baxendale IR. Org. Biomol. Chem. 2015; 13: 9907
7d Raju BR, Saikia AK. Molecules 2008; 13: 1942
7e Quintavalla A. Curr. Med. Chem. 2018; 25: 917

8 Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540

9a Tietze LF. Chem. Rev. 1996; 96: 115
9b Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
9c Nicolaou KC, Chen JS. Chem. Soc. Rev. 2009; 38: 2993
9d Chanda T, Zhao JC.-G. Adv. Synth. Catal. 2018; 360: 2
9e Pellissier H. Chem. Rev. 2013; 113: 442
9f Pellissier H. Adv. Synth. Catal. 2012; 354: 237

10 Tietze LF, Brasche G, Gericke K. In Domino Reactions in Organic Synthesis 2006
11 Liu X.-L, Zuo X, Wang J.-X, Chang S.-q, Weib Q.-D, Zhou Y. Org. Chem. Front. 2019; 6: 1485

12a Amata E, Bland ND, Campbell RK, Pollastri MP. Tetrahedron Lett. 2015; 56: 2832
12b Chande MS, Barve PA, Suryanarayan V. J. Heterocycl. Chem. 2007; 44: 49
12c Leng H.-J, Li Q.-Z, Zeng R, Dai Q.-S, Zhu H.-P, Liu Y, Huang W, Han B, Li J.-L. Adv. Synth. Catal. 2018; 360: 229
12d Han B, Xu S, Wang P. CN 104610148, 2015

13 Rana NK, Shukla K, Mahto P, Jha RK, Singh VK. Tetrahedron 2018; 74: 5270

For reviews, see:

14a Lalit K, Chandresh T, Vivek S. Int. J. Res. Pharm. Sci. 2012; 2: 13
14b Hamama WS, El-Gohary HG, Kuhnert N, Zoorob HH. Curr. Org. Chem. 2012; 16: 373
14c Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984

For review, see:

15a Yu B, Zheng Y.-C, Shi X.-J, Qi P.-P, Liu H.-M. Med. Chem. 2016; 16: 1315
15b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
15c Badillo JJ, Hanhan NV, Franz AK. Curr. Opin. Drug Discovery Dev. 2010; 13: 758
15d Yang Y.-T, Zhu J.-F, Liao GC, Xu H.-J, Yu B. Curr. Med. Chem. 2018; 25: 2233
15e Panda SS, Jones RA, Bachawala P, Mohapatra PP. Med. Chem. 2017; 17: 1515
15f Pavlovska TL, Redkin RG, Lipson VV, Atamanuk DV. Mol. Diversity 2016; 20: 299
15g Yu B, Yu D.-Q, Liu H.-M. Eur. J. Med. Chem. 2015; 97: 673
15h Yu B, Yu Z, Qi P.-P, Yu D.-Q, Liu H.-M. Eur. J. Med. Chem. 2015; 95: 35

16 Chaudhari PD, Hong B.-C, Wen C.-L, Lee G.-H. ACS Omega 2019; 4: 655

17a Takizawa S, Kishi K, Kusaba M, Jianfei B, Suzuki T, Sasai H. Heterocycles 2017; 95
17b Ding L.-Z, Zhong T.-S, Wu H, Wang Y.-M. Eur. J. Org. Chem. 2014; 2014: 5139
17c Monari M, Montroni E, Nitti A, Lombardo M, Trombini C, Quintavalla A. Chem. Eur. J. 2015; 21: 11038
17d Wei Q, Gong L.-Z. Org. Lett. 2010; 12: 1008
17e Bencivenni G, Wu L.-Y, Mazzanti A, Giannichi B, Pesciaioli F, Song M.-P, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7200

18 Zhao B.-L, Du D.-M. Chem. Commun. 2016; 52: 6162

19a Li C.-Y, Xiang M, Song X.-J, Zou Y, Huang Z.-C, Li X, Tian F, Wang L.-X. Org. Biomol. Chem. 2020; 18: 9511
19b Wang Q.-L, Cai T, Zhou J, Tian F, Xu X.-Y, Wang L.-X. Chem. Commun. 2015; 51: 10726
19c Liu X.-L, Zhou G, Gong Y, Yao Z, Zuo X, Zhang W.-H, Zhou Y. Org. Lett. 2019; 21: 2528

20 Hayashi Y, Nagai K, Umemiya S. Eur. J. Org. Chem. 2019; 2019: 678
21 Meninno S, Overgaard J, Lattanzi A. Synthesis 2017; 49: 1509

22a Maebashi M, Makino Y, Furukawa Y, Ohinata K, Kimura S, Sato T. J. Clin. Biochem. Nutr. 1993; 14: 211
22b Zempleni J, Wijeratne SS. K, Hassan YI. Biofactors 2009; 35: 36
22c Yoshimura Y, Watanabe M, Satoh H, Ashida N, Ijichi K, Sakata S, Machida H, Matsuda A. J. Med. Chem. 1997; 40: 2177
22d Johnson JW, Evanoff DP, Savard ME, Lange G, Ramadhar TR, Assoud A, Taylor NJ, Dmitrienko GI. J. Org. Chem. 2008; 73: 6970
22e Morita N, Krause N. Angew. Chem. Int. Ed. 2006; 45: 1897 ; and cited references

23 Huang Y, Zheng C, Chai Z, Zhao G. Adv. Synth. Catal. 2014; 356: 579
24 Duan J, Cheng J, Li B, Qi F, Li P. Eur. J. Org. Chem. 2015; 2015: 6130

Reviews:

25a Mosey RA, Fisk JS, Tepe JJ. Tetrahedron: Asymmetry 2008; 19: 2755
25b Alba A.-NR, Rios R. Chem. Asian J. 2011; 6: 720

26 Weber M, Frey W, Peters R. Chem. Eur. J. 2013; 19: 8342
27 Zhao S, Lin J.-B, Zhao Y.-Y, Liang Y.-M, Xu P.-F. Org. Lett. 2014; 16: 1802
28 Wang S, Jiang Y, Wu S, Dong G, Miao Z, Zhang W, Sheng C. Org. Lett. 2016; 18: 1028
29 Ji C, Wang S, Chen S, He S, Jiang Y, Miao Z, Li J, Sheng C. Bioorg. Med. Chem. 2017; 25: 5268
30 Reddy GM, Ko C.-T, Hsieh K.-H, Lee C.-J, Das U, Lin W. J. Org. Chem. 2016; 81: 2420
31 Luo N.-h, Sun X, Wei W.-t, Zhang X.-j, Yan M. Tetrahedron: Asymmetry 2013; 24: 402
32 Ričko S, Testen Ž, Ciber L, Požgan F, Štefane B, Brodnik H, Svete J, Grošelj U. Catalysts 2020; 10: 1211
33 Tang Q.-G, Cai S.-L, Wang C.-C, Lin G.-Q, Sun X.-W. Org. Lett. 2020; 22: 3351

34a Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B. J. Org. Chem. 1991; 56: 6527
34b Rottmann M, McNamara C, Yeung BK. S, Lee MC. S, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt E, Beck H.-P, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
34c Zhou F, Liu YL, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
34d Larsen TO, Frydenvang K, Frisvad JC, Christophersen C. J. Nat. Prod. 1998; 61: 1154
34e Ariza MR, Larsen TO, Petersen BO, Duus J, Christophersen C, Barrero AF. J. Nat. Prod. 2001; 64: 1590
34f Hibino S, Choshi T. Nat. Prod. Rep. 2001; 18: 66
34g Wu M, Ma D. Angew. Chem. Int. Ed. 2013; 52: 9759
34h Chen L, Ding QJ, Liu JJ, Yang S, Zhang ZM. US 2007213341 A1, 2007
34i Ding QJ, Liu JJ, Zhang ZM. WO 2007104714 A1, 2007

35a Li J.-H, Wen H, Liu L, Du D.-M. Eur. J. Org. Chem. 2016; 2016: 2492
35b Li J.-H, Du D.-M. Chem. Asian J. 2014; 9: 3278
35c Yang W, Du D.-M. Chem. Commun. 2013; 49: 8842
35d Zhao B.-L, Du D.-M. Asian J. Org. Chem. 2015; 4: 1120

36 Huang Y.-M, Zheng C.-W, Zhao G. RSC Adv. 2013; 3: 16999
37 Mao H, Lin A, Tang Y, Shi Y, Hu H, Cheng Y, Zhu C. Org. Lett. 2013; 15: 4062
38 Deng Y, Sun S, Wang Y, Jia P, Li W, Wang K, Yan W. Adv. Synth. Catal. 2022; 364: 811
39 Grošelj U, Ciber L, Gnidovec J, Testen Ž, Požgan F, Štefane B, Tavčar G, Svete J, Ričko S. Adv. Synth. Catal. 2019; 361: 5118

For selected examples of biologicaly active pyrrolin-4-ones see:

40a Williams RM, Kwast E, Coffman H, Glinka T. Appl. Environ. Microbiol. 1989; 111: 3065
40b Bowen C, Malcolm S, Melnick L, Xie L. WO 2013070659 A1, 2013
40c Murugesan D, Mital A, Kaiser M, Shackleford DM, Morizzi J, Katneni K, Campbell M, Hudson A, Charman SA, Yeates C, Gilbert IH. J. Med. Chem. 2013; 56: 2975
40d Murugesan D, Kaiser M, White KL, Norval S, Riley J, Wyatt PG, Charman SA, Read KD, Yeates C, Gilbert IH. ChemMedChem 2013; 8: 1537
40e Smith AB, Hirschmann R, Pasternak A, Yao W, Sprengeler PA, Holloway MK, Kuo LC, Chen Z, Darke PL, Schleif WA. J. Med. Chem. 1997; 40: 2440

41a Bharkavi C, Vivek SK, Perumal S. Synlett 2015; 26: 1665
41b Kumar SV, Prasanna P, Perumal S. Tetrahedron Lett. 2013; 54: 6651
41c Mahajan S, Chauhan P, Blümel M, Puttreddy R, Rissanen K, Raabe G, Enders D. Synthesis 2016; 48: 1131
41d Kaya U, Mahajan S, Schöbel J.-H, Valkonen A, Rissanen K, Enders D. Synthesis 2016; 48: 4091
41e Liang J.-J, Pan J.-Y, Xu D.-C, Xie J.-W. Tetrahedron Lett. 2014; 55: 6335
41f Hu Y.-J, Wang X.-B, Li S.-Y, Xie S.-S, Wang KD. G, Kong L.-Y. Tetrahedron Lett. 2015; 56: 105
41g Gui Y.-Y, Yang J, Qi L.-W, Wang X, Tian F, Li X.-N, Peng L, Wang L.-X. Org. Biomol. Chem. 2015; 13: 6371
41h Duan S.-W, Li Y, Liu Y.-Y, Zou Y.-Q, Shi D.-Q, Xiao W.-J. Chem. Commun. 2012; 48: 5160

42 Tan B, Candeias NR, Barbas CF. III. Nat. Chem. 2011; 3: 473
43 Huang X.-F, Liu Z.-M, Geng Z.-C, Zhang S.-Y, Wang Y, Wang X.-W. Org. Biomol. Chem. 2012; 10: 8794

44a Anwar S, Li SM, Chen K. Org. Lett. 2014; 16: 2993
44b Ghosh AK, Zhou B. Tetrahedron Lett. 2013; 54: 2311

45 Xu J, Hu L, Hu H, Ge S, Liu X, Feng X. Org. Lett. 2019; 21: 1632

46a Ke B, Tian M, Li J, Liu B, He G. Med. Res. Rev. 2016; 36: 983
46b Kumar V, Kaur K, Gupta GK, Sharma AK. Eur. J. Med. Chem. 2013; 69: 735
46c Varvounis G. Adv. Heterocycl. Chem. 2009; 98: 143
46d Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893

47 Zhou P, Cai Y, Lin L, Lian X, Xia Y, Liu X, Feng X. Adv. Synth. Catal. 2015; 357: 695
48 Sun J, Jiang C, Zhou Z. Eur. J. Org. Chem. 2016; 2016: 1165

49a Qi L.-W, Wang L.-L, Peng L, Jia L.-N, Tian F, Xu X.-Y, Wang L.-X. Tetrahedron 2013; 69: 9303
49b Wang L.-L, Peng L, Bai J.-F, Huang Q.-C, Xu X.-Y, Wang L.-X. Chem. Commun. 2010; 46: 8064

50 Duan J, Cheng J, Li P. Org. Chem. Front. 2015; 2: 1048
51 Arai T, Miyazaki T, Ogawa H, Masu H. Org. Lett. 2016; 18: 5824
52 Wang S, Chen S, Guo Z, He S, Zhang F, Liu X, Chen W, Zhang S, Sheng C. Org. Biomol. Chem. 2018; 16: 625
53 Companyo X, Zea A, Alba A.-NR, Mazzanti A, Moyano A, Rios R. Chem. Commun. 2010; 46: 6953
54 Zeng X, Ni Q, Raabe G, Enders D. Angew. Chem. Int. Ed. 2013; 52: 2977
55 Géant P.-Y, Urban M, Remeš M, Císařová I, Veselý J. Eur. J. Org. Chem. 2013; 2013: 7979
56 Kuan H.-H, Chien C.-H, Chen K. Org. Lett. 2013; 15: 2880
57 Jiang K, Jia Z.-J, Yin X, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 2766
58 Ren W, Wang X.-Y, Li J.-J, Tian M, Liu J, Ouyanga L, Wang J.-H. RSC Adv. 2017; 7: 1863
59 Chaudhari PD, Hong B.-C, Lee G.-H. Org. Lett. 2017; 19: 6112
60 Bai M, Chen Y.-Z, Cui B.-D, Xu X.-Y, Yuan W.-C. Tetrahedron 2019; 75: 2155
61 Yang P, Wang X, Chen F, Zhang Z.-B, Chen C, Peng L, Wang L.-X. J. Org. Chem. 2017; 82: 3908
62 Cui B.-D, Li S.-W, Zuo J, Wu Z.-J, Zhang X.-M, Yuan W.-C. Tetrahedron 2014; 70: 1895
63 Cao Y, Jiang X, Liu L, Shen F, Zhang F, Wang R. Angew. Chem. Int. Ed. 2011; 50: 9124
64 Liu L, Zhong Y, Zhang P, Jiang X, Wang R. J. Org. Chem. 2012; 77: 10228
65 Zhu W.-R, Chen Q, Lin N, Chen K.-B, Zhang Z.-W, Fang G, Weng J, Lu G. Org. Chem. Front. 2018; 5: 1375
66 Tan F, Cheng H.-G, Feng B, Zou Y.-Q, Duan S.-W, Chen J.-R, Xiao W.-J. Eur. J. Org. Chem. 2013; 2013: 2071
67 Fu Z.-K, Pan J.-Y, Xu D.-C, Xie J.-W. RSC Adv. 2014; 4: 51548
68 Hu J.-L, Sha F, Li Q, Wu X.-Y. Tetrahedron 2018; 74: 7148

69a Li T.-Z, Xie J, Jiang Y, Sha F, Wu X.-Y. Adv. Synth. Catal. 2015; 357: 3507
69b Xie J, Xing X.-Y, Sha F, Wub Z.-Y, Wu X.-Y. Org. Biomol. Chem. 2016; 14: 8346
69c Xie J, Xing W.-L, Sha F, Wu X.-Y. Eur. J. Org. Chem. 2016; 2016: 3983

70 Pan F.-F, Yu W, Qi Z.-H, Qiao C, Wang X.-W. Synthesis 2014; 46: 1143
71 Jiang X, Sun Y, Yao J, Cao Y, Kai M, He N, Zhang X, Wang Y, Wang R. Adv. Synth. Catal. 2012; 354: 917
72 Zhu X.-Q, Wu J.-S, Xie J.-W. Tetrahedron 2016; 72: 8327
73 Chennapuram M, Owolabi IA, Seki C, Okuyama Y, Kwon E, Uwai K, Tokiwa M, Takeshita M, Nakano H. ACS Omega 2018; 3: 11718
74 Zhang J, Cheng C, Wang D, Miao Z. J. Org. Chem. 2017; 82: 10121
75 Zhou H.-J, Zhou W, Liu X.-L, Tian Y.-P, Wang J.-X, Zhou Y. Synthesis 2020; 52: 3047
76 Huang Z, Zou Y, Xiang M, Li C, Li X, Tian F, Wang L. Org. Lett. 2021; 23: 2227
77 Yin X, Zheng Y, Feng X, Jiang K, Wei X.-Z, Gao N, Chen Y.-C. Angew. Chem. Int. Ed. 2014; 53: 6245
78 He X.-L, Xiao Y.-C, Du W, Chen Y.-C. Chem. Eur. J. 2015; 21: 3443
79 Zhi Y, Zhao K, von Essen C, Rissanen K, Enders D. Synlett 2017; 28: 2876
80 Song Y.-X, Du D.-M. J. Org. Chem. 2018; 83: 9278
81 Lin Y, Song Y.-X, Du D.-M. Adv. Synth. Catal. 2019; 361: 1064
82 Zhao B.-L, Du D.-M. Adv. Synth. Catal. 2019; 361: 3412
83 Wu H, Wang Y.-M. Chem. Eur. J. 2014; 20: 5899
84 Jacob RG, Perin G, Botteselle GV, Lenardão EJ. Tetrahedron Lett. 2003; 44: 6809
85 Hodík T, Schneider C. Chem. Eur. J. 2018; 24: 18082
86 Zhou J, Wang Q.-L, Peng L, Tian F, Xu X.-Y, Wang L.-X. Chem. Commun. 2014; 50: 14601
87 Pesciaioli F, Righi P, Mazzanti A, Bartoli G, Bencivenni G. Chem. Eur. J. 2011; 17: 2842
88 Sun W, Zhu G, Wu C, Hong L, Wang R. Chem. Eur. J. 2012; 18: 6737
89 Goudedranche S, Bugaut X, Constantieux T, Bonne D, Rodriguez J. Chem. Eur. J. 2014; 20: 410

90a Kumarswamyreddy N, Kesavan V. Org. Lett. 2016; 18: 1354
90b Yao W, Pan L, Wu Y, Ma C. Org. Lett. 2010; 12: 2422
90c Wang X, Yao W, Yao Z, Ma C. J. Org. Chem. 2012; 77: 2959

91a Albertshofer K, Tan B, Barbas CF. III. Org. Lett. 2012; 14: 1834
91b Wang S, Guo Z, Chen S, Jiang Y, Zhang F, Liu X, Chen W, Sheng C. Chem. Eur. J. 2018; 24: 62

92a Zhao K, Zhi Y, Shu T, Valkonen A, Rissanen K, Enders D. Angew. Chem. Int. Ed. 2016; 55: 12104
92b Ye Z, Bai L, Bai Y, Gan Z, Zhou H, Pan T, Yu Y, Zhou J. Tetrahedron 2019; 75: 682

93 You Y, Cui B.-D, Zhou M.-Q, Zuo J, Zhao J.-Q, Xu X.-Y, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2015; 80: 5951
94 Palomba M, Rossi L, Sancineto L, Tramontano E, Corona A, Bagnoli L, Santi C, Pannecouque C, Tabarrinia O, Marini F. Org. Biomol. Chem. 2016; 14: 2015
95 Zhang K, Meazza M, Dočekal V, Light ME, Veselý J, Rios R. Eur. J. Org. Chem. 2017; 2017: 1749

For review see:

96a Arend M, Westermann B, Risch N. Angew. Chem. Int. Ed. 1998; 37: 1044
96b Roman G. Eur. J. Med. Chem. 2015; 89: 743
96c Heravi MM, Zadsirjan V, Savadjani ZB. Curr. Org. Chem. 2014; 18: 2857
96d Greco SJ, Lacerda VJr, dos Santos RB. Aldrichimica Acta 2011; 44: 15
96e Allochio Filho JF, Lemos BC, de Souza AS, Pinheiro S, Greco SJ. Tetrahedron 2017; 73: 6977

97 Zhao K, Zhi Y, Li X, Puttreddy R, Rissanenb K, Enders D. Chem. Commun. 2016; 52: 2249
98 Huang X, Zhang Y.-R, Li X.-S, Xu D.-C, Xie J.-W. Tetrahedron Lett. 2013; 54: 5857
99 Bai M, Cui B.-D, Zuo J, Zhao J.-Q, You Y, Chen Y.-Z, Xu X.-Y, Zhang X.-M, Yuan W.-C. Tetrahedron 2015; 71: 949
100 Ping X.-N, Chen W, Lu X.-Y, Xie J.-W. ARKIVOC 2016; (vi): 274
101 Zhao B.-L, Du D.-M. Org. Lett. 2018; 20: 3797

For review see:

102a Han Y.-F, Xia M. Curr. Org. Chem. 2010; 14: 379
102b Voskressensky LG, Festa AA, Varlamov AV. Tetrahedron 2014; 70: 551
102c Majumdar KC, Taher A, Nandi RK. Tetrahedron 2012; 68: 5693

103 Ramachary DB, Chowdari NS, Barbas CF. III. Synlett 2003; 1910
104 Ramachary DB, Anebouselvy K, Chowdari NS, Barbas CF. III. J. Org. Chem. 2004; 69: 5838
105 Chen W.-B, Wu Z.-J, Pei Q.-L, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2010; 12: 3132
106 Zhao H.-W, Li B, Tian T, Meng W, Yang Z, Song X.-Q, Chen X.-Q, Pang H.-L. Eur. J. Org. Chem. 2015; 2015: 3320
107 Miao Y.-H, Hua Y.-Z, Wang M.-C. Org. Biomol. Chem. 2019; 17: 7172
108 Du T, Du F, Ning Y, Peng Y. Org. Lett. 2015; 17: 1308
109 He Y.-H, He T, Guo J.-T, Li R, Xiang Y, Yang D.-C, Guan Z. Catal. Sci. Technol. 2016; 6: 2239
110 Thanki N, Umrania Y, Thornton JM, Goodfellow JM. J. Mol. Biol. 1991; 221: 669
111 Dee DR, Filonowicz S, Horimoto Y, Yada RY. Biochim. Biophys. Acta, Proteins Proteomics 2009; 1794: 1795
112 Peng J, Huang X, Jiang L, Cui H.-L, Chen Y.-C. Org. Lett. 2011; 13: 4584
113 Shen G.-L, Sun J, Yan C.-G. Org. Biomol. Chem. 2015; 13: 10929
114 Mal K, Ray S, Maity S, Nurjamal K, Ghosh P, Brahmachari G, Mukhopadhyay C. ChemistrySelect 2021; 6: 1263
115 Chithiraikumar C, Ponmuthu KV, Harikrishnan M, Malini N, Sepperumal M, Siva A. Res. Chem. Intermed. 2021; 47: 895
116 Toffano M, Guillot R, Bournaud C, Brière J.-F, Vo-Thanh G. Adv. Synth. Catal. 2021; 363: 4452
117 Pellissier H. Adv. Synth. Catal. 2019; 361: 1733
118 Pellissier H. Org. Prep. Proced. Int. 2019; 51: 311
119 Tan F, Lu L.-Q, Yang Q.-Q, Guo W, Bian Q, Chen J.-R, Xiao W.-J. Chem. Eur. J. 2014; 20: 3415
120 Zhao J.-Q, Wu Z.-J, Zhou M.-Q, Xu X.-Y, Zhang X.-M, Yuan W.-C. Org. Lett. 2015; 17: 5020
121 Hanhan NV, Ball-Jones NR, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2012; 51: 989
122 Ball-Jones NR, Badillo JJ, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2014; 53: 9462
123 Li Z, Shi Y. Org. Lett. 2015; 17: 5752
124 Cao W, Liu X, Guo J, Lin L, Feng X. Chem. Eur. J. 2015; 21: 1632
125 Zhao X, Liu X, Mei H, Guo J, Lin L, Feng X. Angew. Chem. Int. Ed. 2015; 54: 4032
126 Zhao X, Liu X, Xiong Q, Mei H, Ma B, Lin L, Feng X. Chem. Commun. 2015; 51: 16076
127 Kato S, Kanai M, Matsunaga S. Chem. Asian J. 2013; 8: 1768
128 Fang W, Presset M, Guérinot A, Bour C, Bezzenine-Lafollée S, Gandon V. Chem. Eur. J. 2014; 20: 5439
129 Hack D, Dîrr AB, Deckers K, Chauhan P, Seling N, Rîbenach L, Mertens L, Raabe G, Schoenebeck F, Enders D. Angew. Chem. Int. Ed. 2016; 55: 1797
130 Putatunda S, Alegre-Requena JV, Meazza M, Franc M, Rohaľová D, Vemuri P, Císařová I, Herrera RP, Rios R, Veselý J. Chem. Sci. 2019; 10: 4107
131 Meazza M, Kamlar M, Jašíková L, Formánek B, Mazzanti A, Roithová J, Veselý J, Rios R. Chem. Sci. 2018; 9: 6368
132 Afewerki S, Ma G, Ibrahem I, Liu L, Sun J, Córdova A. ACS Catal. 2015; 5: 1266
133 Chogii I, Njardarson JT. Angew. Chem. Int. Ed. 2015; 54: 13706
134 Arunprasath D, Bala BD, Sekar G. Org. Lett. 2017; 19: 5280
135 Liu J.-G, Chen W.-W, Gu C.-X, Xu B, Xu M.-H. Org. Lett. 2018; 20: 2728
136 Beltran F, Miesch L. Org. Lett. 2019; 21: 1569
137 Beltran F, Andna L, Miesch L. Org. Chem. Front. 2019; 6: 373
138 Li T.-Z, Jiang Y, Guan Y.-Q, Sha F, Wu X.-Y. Chem. Commun. 2014; 50: 10790
139 Han J.-L, Chang C.-H. Chem. Commun. 2016; 52: 2322
140 Du D, Hu Z, Jin J, Lu Y, Tang W, Wang B, Lu T. Org. Lett. 2012; 14: 1274
141 Sánchez-Larios E, Holmes JM, Daschner CL, Gravel M. Org. Lett. 2010; 12: 5772
142 Sun FG, Huang XL, Ye S. J. Org. Chem. 2010; 75: 273
143 Yadav A, Banerjee J, Arupula SK, Mobin SM, Samanta S. Asian J. Org. Chem. 2018; 7: 1595
144 Hajra S, Bhosale SS, Hazra A, Kanaujia N. Org. Biomol. Chem. 2019; 17: 8140
145 Xiao B.-X, Jiang B, Song X, Du W, Chen Y.-C. Chem. Commun. 2019; 55: 3097
146 Wang Y, Wang X, Lin J, Yao B, Wang G, Zhao Y, Zhang X, Lin B, Liu Y, Cheng M, Liu Y. Adv. Synth. Catal. 2018; 360: 1483

147a Barluenga J, Fañanás-Mastral M, Aznar F, Valdés C. Angew. Chem. Int. Ed. 2008; 47: 6594
147b Haibach MC, Seidel D. Angew. Chem. Int. Ed. 2014; 53: 5010

148 Zheng C, You S. Acc. Chem. Res. 2020; 53: 974