Chiral Phosphoric Acid Catalyzed Asymmetric Cycloadditions: from Alkenes to Alkynes

Liu-Yang Wang; Lan Yang; Jie Chen; Ling Zhou

doi:10.1055/a-2003-2276

Synlett, Table of Contents

Synlett 2023; 34(11): 1200-1214
DOI: 10.1055/a-2003-2276

account

Chiral Phosphoric Acid Catalyzed Asymmetric Cycloadditions: from Alkenes to Alkynes

Liu-Yang Wang‡

,

Lan Yang‡

,

Jie Chen∗

,

Ling Zhou∗

Abstract

All articles of this category

Abstract

Organocatalytic asymmetric cycloaddition reactions are the foundation for the construction of important cyclic molecules in synthetic chemistry and biochemistry. As a result, organic catalysts, in particular chiral phosphoric acid, entice researchers from all over the world to design and develop asymmetric cycloaddition reactions. In this Account, we discuss CPA-catalyzed [3+2] and [4+2] cycloaddition of alkenes and some further transformations from the cycloadducts, as well as several mechanisms related to these cycloadditions. All kinds of enantioenriched carbocycles and heterocycles with stereogenic centers could be synthesized efficiently. Recent advances in CPA-catalyzed cycloaddition of alkynes to generate axially chiral compounds are also discussed.

1 Introduction

2 CPA-Catalyzed [3+2] Cycloaddition of Alkenes

3 CPA-Catalyzed [4+2] Cycloaddition of Alkenes

4 CPA-Catalyzed Cycloaddition of Alkynes

5 Conclusions

Key words

chiral phosphoric acid - organocatalysis - cycloaddition - alkenes - alkynes

Full Text

References

References

1a Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
1b Perreault S, Rovis T. Chem. Soc. Rev. 2009; 38: 3149
1c Harmata M. Adv. Synth. Catal. 2006; 348: 2297
1d Zhou Y.-Y, Li J, Ling L, Liao S.-H, Sun X.-L, Li Y.-X, Wang L.-J, Tang Y. Angew. Chem. Int. Ed. 2013; 52: 1452

2a Ylijoki KE. O, Stryker JM. Chem. Rev. 2013; 113: 2244
2b Xing Y, Wang N.-X. Coord. Chem. Rev. 2012; 256: 938
2c Xie M, Liu X, Wu X, Cai Y, Lin L, Feng X. Angew. Chem. Int. Ed. 2013; 52: 5604
2d Eschenbrenner-Lux V, Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2014; 53: 11146

3a Sakakura A, Ishihara K. Chem. Soc. Rev. 2011; 40: 163
3b Biswas S, Parsutkar MM, Jing SM, Pagar VV, Herbort JH, RajanBabu TV. Acc. Chem. Res. 2021; 54: 4545
3c Johnson JS, Evans DA. Acc. Chem. Res. 2000; 33: 325
3d Chen W, Yang D. Chin. J. Org. Chem. 2016; 36: 2075

4a Klier L, Tur F, Poulsen PH, Jørgensen KA. Chem. Soc. Rev. 2017; 46: 1080
4b Liu X, Zheng H, Xia Y, Lin L, Feng X. Acc. Chem. Res. 2017; 50: 2621

5a Laina-Martin V, Fernandez-Salas JA, Aleman J. Chem. Eur. J. 2021; 27: 12509
5b Ma Y.-H, He X.-Y, Yang Q.-Q, Boucherif A, Xuan J. Asian J. Org. Chem. 2021; 10: 1233
5c Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713

6a Woldegiorgis AG, Suleman M, Lin X. Eur. J. Org. Chem. 2022; e202200624
6b Held FE, Grau D, Tsogoeva SB. Molecules 2015; 20: 16103

7a Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566
7b Uraguchi D, Terada M. J. Am. Chem. Soc. 2004; 126: 5356

8a Akiyama T. Chem. Rev. 2007; 107: 5744
8b Parmar D, Sugiono E, Raja S, Rueping MJ. Chem. Rev. 2014; 114: 9047
8c Terada M. Synthesis 2010; 1929
8d Maji R, Mallojjala SC, Wheeler SE. Chem. Soc. Rev. 2018; 47: 1142
8e Xia Z.-L, Xu-Xu Q.-F, Zheng C, You S.-L. Chem. Soc. Rev. 2020; 49: 286
8f Shao Y.-D, Cheng D.-J. ChemCatChem 2021; 13: 1271

9 Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047

10a Li W, Zhou L, Zhang J. Chem. Eur. J. 2016; 22: 1558
10b Feng H.-X, Wang Y.-Y, Chen J, Zhou L. Adv. Synth. Catal. 2015; 357: 940
10c Xu W.-L, Zhang H, Hu Y.-L, Yang H, Chen J, Zhou L. Org. Lett. 2018; 20: 5774

11a Xu W.-L, Tang L, Ge C.-Y, Chen J, Zhou L. Adv. Synth. Catal. 2019; 361: 2268
11b Xu W.-L, Hu W, Zhao W.-M, Wang M, Chen J, Zhou L. Org. Lett. 2020; 22: 7169
11c Sharif A, Sun H.-R, Xu W.-L, Gou B.-B, Yang L, Li Y, Chen J, Zhou L. Org. Lett. 2022; 24: 4316

12a Zhao M, Zhang Y.-T, Chen J, Zhou L. Asian J. Org. Chem. 2018; 7: 54
12b Zhao M, Chen J, Yang H, Zhou L. Chem. Eur. J. 2017; 23: 2783
12c Sun H.-R, Zhao Q, Yang H, Yang S, Gou B.-B, Chen J, Zhou L. Org. Lett. 2019; 21: 7143

13a Yang H, Chen J, Zhou L. Chem. Asian J. 2020; 15: 2939
13b Quinonero O, Jean M, Vanthuyne N, Roussel C, Bonne D, Constantieux T, Bressy C, Bugaut X, Rodriguez J. Angew. Chem. Int. Ed. 2016; 55: 1401
13c Raut VS, Jean M, Vanthuyne N, Roussel C, Constantieux T, Bressy C, Bugaut X, Bonne D, Rodriguez J. J. Am. Chem. Soc. 2017; 139: 2140
13d Yang H, Xu W.-L, Zeng X.-Y, Chen J, Yu L, Zhou L. Org. Lett. 2021; 23: 9315

14a Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
14b Adrio J, Carretero JC. Chem. Commun. 2019; 55: 11979
14c Cheng F, Kalita SJ, Zhao Z.-N, Yang X, Zhao Y, Schneider U, Shibata N, Huang Y.-Y. Angew. Chem. Int. Ed. 2019; 58: 16637

15 Chen X.-H, Zhang W.-Q, Gong L.-Z. J. Am. Chem. Soc. 2008; 130: 5652
16 Chen X.-H, Wei Q, Luo S.-W, Xiao H, Gong L.-Z. J. Am. Chem. Soc. 2009; 131: 13819
17 Liao L, Shu C, Zhang M, Liao Y, Hu X, Zhang Y, Wu Z, Yuan W, Zhang X. Angew. Chem. Int. Ed. 2014; 53: 10471
18 Zhu R.-Y, Wang C.-S, Zheng J, Shi F, Tu S.-J. J. Org. Chem. 2014; 79: 9305
19 Sun X.-X, Zhang H.-H, Li G.-H, Meng L, Shi F. Chem. Commun. 2016; 52: 2968
20 Wang Y, Wang Q, Zhu J. Chem. Eur. J. 2016; 22: 8084
21 Gelis C, Bekkaye M, Lebée C, Blanchard F, Masson G. Org. Lett. 2016; 18: 3422
22 Li X.-Q, Yang H, Wang J.-J, Gou B.-B, Chen J, Zhou L. Chem. Eur. J. 2017; 23: 5381
23 Feng W, Yang H, Wang Z, Gou B.-B, Chen J, Zhou L. Org. Lett. 2018; 20: 2929
24 Qi L.-W, Mao J.-H, Zhang J, Tan B. Nat. Chem. 2018; 10: 58
25 Li C, Xu D.-N, Ma C, Mei G.-J, Shi F. J. Org. Chem. 2018; 83: 9190

26a Privileged Chiral Ligands and Catalysts . Zhou Q.-L. Wiley-VCH; Weinheim: 2011
26b Bringmann G, Gulder T, Gulder TA. M, Breuning M. Chem. Rev. 2011; 111: 563
26c Kumarasamy E, Raghunathan R, Sibi MP, Sivaguru J. Chem. Rev. 2015; 115: 11239
26d Cheng JK, Xiang S.-H, Li S, Ye L, Tan B. Chem. Rev. 2021; 121: 4805

27a Wang Y.-B, Tan B. Acc. Chem. Res. 2018; 51: 534
27b Li T.-Z, Liu S.-J, Tan W, Shi F. Chem. Eur. J. 2020; 26: 15779
27c He X.-L, Wang C, Wen Y.-W, Wang Z, Qian S. ChemCatChem 2021; 13: 3547
27d Zhang H.-H, Shi F. Acc. Chem. Res. 2022; 55: 2562

28 Hu Y.-L, Wang Z, Yang H, Chen J, Wu Z.-B, Lei Y, Zhou L. Chem. Sci. 2019; 10: 6777
29 Xu W.-L, Zhao W.-M, Zhang R.-X, Chen J, Zhou L. Chem. Sci. 2021; 12: 14920

30a Lin L, Liu X, Feng X. Synlett 2007; 2147
30b Li J.-L, Liu T.-Y, Chen Y.-C. Acc. Chem. Res. 2012; 45: 1491
30c Jiang X, Wang R. Chem. Rev. 2013; 113: 5515
30d Masson G, Lalli C, Benohoud M, Dagousset G. Chem. Soc. Rev. 2013; 42: 902
30e Fochi M, Caruana L, Bernardi L. Synthesis 2014; 46: 135

31 Itoh J, Fuchibe K, Akiyama T. Angew. Chem. Int. Ed. 2006; 45: 4796
32 Akiyama T, Tamura Y, Itoh J, Morita H, Fuchibe K. Synlett 2006; 141
33 Akiyama T, Morita H, Fuchibe K. J. Am. Chem. Soc. 2006; 128: 13070
34 Liu H, Dagousset G, Masson G, Retailleau P, Zhu J. J. Am. Chem. Soc. 2009; 131: 4598
35 He L, Laurent G, Retailleau P, Folléas B, Brayer J.-L, Masson G. Angew. Chem. Int. Ed. 2013; 52: 11088
36 Bergonzini G, Gramigna L, Mazzanti A, Fochi M, Bernardi L, Ricci A. Chem. Commun. 2010; 46: 327
37 Hatano M, Goto Y, Izumiseki A, Akakura M, Ishihara K. J. Am. Chem. Soc. 2015; 137: 13472
38 Hatano M, Sakamoto T, Mochizuki T, Ishihara K. Asian J. Org. Chem. 2019; 8: 1061
39 Zhao Q, Li Y, Zhang Q.-X, Cheng J.-P, Li X. Angew. Chem. Int. Ed. 2021; 60: 17608
40 Bisag GD, Pecorari D, Mazzanti A, Bernardi L, Fochi M, Bencivenni G, Bertuzzi G, Corti V. Chem. Eur. J. 2019; 25: 15694
41 Wang S.-J, Wang Z, Tang Y, Chen J, Zhou L. Org. Lett. 2020; 22: 8894
42 Momiyama N, Tabuse H, Terada M. J. Am. Chem. Soc. 2009; 131: 12882
43 Zhao J.-J, Sun S.-B, He S.-H, Wu Q, Shi F. Angew. Chem. Int. Ed. 2015; 54: 5460
44 Tu M.-S, Liu S.-J, Zhong C, Zhang S, Zhang H, Zheng Y.-L, Shi F. J. Org. Chem. 2020; 85: 5403
45 Wang Y, Tu M.-S, Yin L, Sun M, Shi F. J. Org. Chem. 2015; 80: 3223
46 Koay WL, Mei G.-J, Lu Y. Org. Chem. Front. 2021; 8: 968
47 Wang Z, Sun J. Org. Lett. 2017; 19: 2334
48 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
49 Feng S, Yang B, Chen T, Wang R, Deng Y.-H, Shao Z. J. Org. Chem. 2020; 85: 5231
50 Pous J, Courant T, Bernadat G, Iorga BI, Blanchard F, Masson G. J. Am. Chem. Soc. 2015; 137: 11950
51 Varlet T, Matišić M, Van Elslande E, Neuville L, Gandon V, Masson G. J. Am. Chem. Soc. 2021; 143: 11611
52 Zhu X.-Q, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2022; 61: e202214925

For selected racemic examples, see:

53a Yang Y, Liu H, Peng C, Wu J, Zhang J, Qiao Y, Wang X.-N, Chang J. Org. Lett. 2016; 18: 5022
53b Bu H.-Z, Li H.-H, Luo W.-F, Luo C, Qian P.-C, Ye L.-W. Org. Lett. 2020; 22: 648
53c Feng Q, Wu A, Zhang X, Song L, Sun J. Chem. Sci. 2021; 12: 7953
53d Zhu C.-F, Chen L.-Q, Hao W.-J, Cui C.-C, Tu S.-J, Jiang B. Org. Lett. 2021; 23: 2654

54 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
55 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