Asymmetric Access to Chiral Sulfinyl Compounds as Bioisosteres of Carbonyl Compounds

Chenxin Wang; Xinyu Wu; Jiapian Huang; Gang Liu; Jie Wu

doi:10.1055/a-2335-8452

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(17): 2648-2654
DOI: 10.1055/a-2335-8452

paper

Bioisosteres

Asymmetric Access to Chiral Sulfinyl Compounds as Bioisosteres of Carbonyl Compounds

Chenxin Wang

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang, 330013, P. R. of China

,

Xinyu Wu

^bInstitute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China

,

Jiapian Huang

^bInstitute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China

,

Gang Liu∗

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang, 330013, P. R. of China

,

Jie Wu∗

^bInstitute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China

^cState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

^dSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The sulfinyl group, as one of the bioisosteres of carbonyl groups, attracts considerable attention in the field of synthetic chemistry. In particular, the asymmetric construction of chiral sulfinyl compounds and their derivatives remains in the early stages of development. Sulfinyl compounds mainly include sulfoxides, sulfinate esters and sulfinamides, according to the different functional groups connected to the sulfur atom. This Review summarizes the fascinating recent progress made over the past decade on the asymmetric synthesis of enantiopure sulfinyl derivatives.

1 Introduction

2 Asymmetric Synthesis of Chiral Sulfoxides

3 Asymmetric Synthesis of Chiral Sulfinate Esters

4 Asymmetric Synthesis of Chiral Sulfinamides

5 Conclusion and Outlook

Key words

sulfinyl - bioisostere - asymmetric synthesis - sulfoxide - sulfinate ester - sulfinamide

Volltext

Referenzen

References

1a Wiesenfeldt MP, Rossi-Ashton JA, Perry IB, Diesel J, Garry OL, Bartels F, Coote SC, Ma X, Yeung CS, Bennett DJ, MacMillan DW. C. Nature 2023; 618: 513
1b Rojas JJ, Croft RA, Sterling AJ, Briggs EL, Antermite D, Schmitt DC, Blagojevic L, Haycock P, White AJ. P, Duarte F, Choi C, Mousseau JJ, Bull JA. Nat. Chem. 2022; 14: 160
1c Huang J, Liu F, Zeng L.-H, Li S, Chen Z, Wu J. Nat. Commun. 2022; 13: 7081
1d Huang J, Liu F, Wu J. Acta Chim. Sin. 2023; 81: 520

2a Andersen KK, Gaffield W, Papanikolaou NE, Foley JW, Perkins RI. J. Am. Chem. Soc. 1964; 86: 5637
2b Evans DA, Faul MM, Colombo L, Bisaha JJ, Clardy J, Cherry D. J. Am. Chem. Soc. 1992; 114: 5977
2c Han Z, Krishnamurthy D, Grover P, Fang K, Senanayake CH. J. Am. Chem. Soc. 2002; 124: 7880
2d Zhang Y, Chitale S, Goyal N, Li G, Han Z, Shen S, Ma S, Grinberg N, Lee H, Lu B, Senanayake CH. J. Org. Chem. 2012; 77: 690
2e Chelouan A, Recio R, Alcudia A, Khiar N, Fernández I. Eur. J. Org. Chem. 2014; 6935
2f Han Z, Meyer AM, Xu Y, Zhang Y, Busch R, Shen S, Grinberg N, Lu B, Krishnamurthy D, Senanayake CH. J. Org. Chem. 2011; 76: 5480
2g Han Z, Herbage MA. H, Mangunuru PR, Xu Y, Zhang L, Reeves JT, Sieber JD, Li Z, DeCroos P, Zhang Y, Li G, Li N, Ma S, Grinberg N, Wang X, Goyal N, Krishnamurthy D, Lu B, Song J, Wang G, Senanayake CH. Angew. Chem. Int. Ed. 2013; 52: 6713
2h Zhang Z, Wang X, Sivaguru P, Wang Z. Org. Chem. Front. 2022; 9: 6063
2i Kumar MR, Farmer PJ. ACS Chem. Biol. 2017; 12: 474
2j Wang Z, Zhang Z, Zhao W, Sivaguru P, Zanoni G, Wang Y, Anderson EA, Bi X. Nat. Commun. 2021; 12: 5244
2k Davies TQ, Tilby MJ, Ren J, Parker NA, Skolc D, Hall A, Duarte F, Willis MC. J. Am. Chem. Soc. 2020; 142: 15445

3a Davis FA, Friedman AJ, Kluger EW. J. Am. Chem. Soc. 1974; 96: 5000
3b Liu G, Cogan DA, Ellman JA. J. Am. Chem. Soc. 1997; 119: 9913
3c Cogan DA, Liu G, Kim K, Backes BJ, Ellman JA. J. Am. Chem. Soc. 1998; 120: 8011
3d Ruano JL. G, Fernandez I, Catalina MP, Cruz AA. Tetrahedron: Asymmetry 1996; 7: 3407
3e Khiar N, Fernandez I, Alcudia F. Tetrahedron Lett. 1994; 35: 5719

4a Fernndez I, Khiar N. Chem. Rev. 2003; 103: 3651
4b Legros J, Dehli JR, Bolm C. Adv. Synth. Catal. 2005; 347: 19
4c Kagan HB. Asymmetric Synthesis of Chiral Sulfoxides. In Organosulfur Chemistry in Asymmetric Synthesis. Toru T, Bolm C. Wiley-VCH; Weinheim: 2009: 1-29
4d Chen J, Zhu G, Wu J. Acta Chim. Sin. 2023; 81: 1609

5a Cotton H, Elebring T, Larsson M, Li L, Sorensen H, von Unge S. Tetrahedron: Asymmetry 2000; 11: 3819
5b Scheper MA, Nikitakis NG, Chaisuparat R, Montaner S, Sauk JJ. Neoplasia 2007; 9: 192
5c Bentley R. Chem. Soc. Rev. 2005; 34: 609
5d El-Aasr M, Fujiwara Y, Takeya T, Tsukamoto S, Ono M, Nakano D, Okawa M, Kinjo J, Yoshimitsu H, Nohara TJ, Ikeda T. J. Nat. Prod. 2010; 73: 1306
5e Wojaczynska E, Wojaczynski J. Chem. Rev. 2010; 110: 4303
5f Williamson KS, Michaelis DJ, Yoon TP. Chem. Rev. 2014; 114: 8016
5g Nohara T, Fujiwara Y, Komota Y, Kondo Y, Saku T, Yamaguchi K, Komohara Y, Takeya M. Chem. Pharm. Bull. 2015; 63: 117
5h Wang X, Zhou W, Xie W, Chen Q, Wu J. Chin. Chem. Lett. 2023; 34: 107984

6 Senanayake CH, Krishnamurthy D, Lu ZH, Han ZX, Gallou I. Aldrichimica Acta 2005; 38: 93

7a Pitchen P, Dunach E, Deshmukh MN, Kagan HB. J. Am. Chem. Soc. 1984; 106: 8188
7b Furia FD, Modena G, Seraglia R. Synthesis 1984; 325

8 Zong L, Ban X, Kee CW, Tan C.-H. Angew. Chem. Int. Ed. 2014; 53: 11849
9 Wang L, Chen M, Zhang P, Li W, Zhang J. J. Am. Chem. Soc. 2018; 140: 3467
10 Zhang Y.-Q, Hu L, Yuwen L, Lu G, Zhang Q.-W. Nat. Catal. 2023; 6: 487
11 Jia T, Zhang M, McCollom SP, Bellomo A, Montel S, Mao J, Dreher SD, Welch CJ, Regalado EL, Williamson RT, Manor BC, Tomson NC, Walsh PJ. J. Am. Chem. Soc. 2017; 139: 8337

12a Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: eaao4798
12b Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
12c Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
12d Davies HM. L, Beckwith RE. J. Chem. Rev. 2003; 103: 2861
12e Davies HM. L, Manning JR. Nature 2008; 451: 417
12f Loup J, Dhawa U, Pesciaioli F, Wencel-Delord J, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 12803
12g Doyle MP, Duffy R, Ratnikov M, Zhou L. Chem. Rev. 2010; 110: 704
12h Yang L, Huang H. Catal. Sci. Technol. 2012; 2: 1099
12i Gao D.-W, Gu Q, Zheng C, You S.-L. Acc. Chem. Res. 2017; 50: 351

13a Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
13b Ackermann L. Chem. Rev. 2011; 111: 1315
13c Hickman AJ, Sanford MS. Nature 2012; 484: 177
13d He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
13e Yang Y.-F, Hong X, Yu J.-Q, Houk KN. Acc. Chem. Res. 2017; 50: 2853
13f He C, Whitehurst WG, Gaunt MJ. Chem 2019; 5: 1031
13g Peneau A, Guillou C, Chabaud L. Eur. J. Org. Chem. 2018; 5777
13h Park J, Chang S. Chem. Asian J. 2018; 13: 1089
13i Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
13j Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
13k Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
13l Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
13m Shan C, Zhu L, Qu L.-B, Bai R, Lan Y. Chem. Soc. Rev. 2018; 47: 7552
13n Gandeepan P, Mueller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
13o Lao Y.-X, Zhang S.-S, Liu X.-G, Jiang C.-Y, Wu J.-Q, Li Q, Huang Z.-S, Wang H. Adv. Synth. Catal. 2016; 358: 2186
13p Xiao W, Wu J. Chin. Chem. Lett. 2023; 34: 107637

14a Vedejs E, Rozners E. J. Am. Chem. Soc. 2001; 123: 2428
14b Bertozzi F, Crotti P, Macchia F, Pineschi M, Feringa BL. Angew. Chem. Int. Ed. 2001; 40: 930
14c Tanaka K, Fu GC. J. Am. Chem. Soc. 2003; 125: 8078
14d Jana CK, Studer A. Angew. Chem. Int. Ed. 2007; 46: 6542
14e Miller LC, Ndungu JM, Sarpong R. Angew. Chem. Int. Ed. 2009; 48: 2398
14f Webster R, Böing C, Lautens M. J. Am. Chem. Soc. 2009; 131: 444
14g Katayev D, Nakanishi M, Burgi T, Kundig EP. Chem. Sci. 2012; 3: 1422
14h Pedroni J, Cramer N. J. Am. Chem. Soc. 2017; 139: 12398
14i Grosheva D, Cramer N. ACS Catal. 2017; 7: 7417

15 Liu W, Yang W, Zhu J, Guo Y, Wang N, Ke J, Yu P, He C. ACS Catal. 2020; 10: 7207
16 Zhu Y.-C, Li Y, Zhang B.-C, Zhang F.-X, Yang Y.-N, Wang X.-S. Angew. Chem. Int. Ed. 2018; 57: 5129
17 Zhou T, Jiang M.-X, Qian P.-F, Yao Q.-J, Xu X.-T, Zhang K, Shi B.-F. Org. Lett. 2021; 23: 7910

18a Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP. J. Steroid Biochem. 1980; 13: 45
18b Ojasoo T, Dore J.-C, Gilbert J, Raynaud JP. J. Med. Chem. 1988; 31: 1160
18c Yolka S, Dunach E, Loiseau M, Lizzani-Cuvelier L, Fellous R, Rochard S, Schippa C, George G. Flavour Fragrance J. 2002; 17: 425
18d Smil DV, Souza FE. S, Fallis AG. Bioorg. Med. Chem. Lett. 2005; 15: 2057
18e Sarrazin E, Shinkaruk S, Pons M, Thibon C, Bennetau B, Darriet P. J. Agric. Food Chem. 2010; 58: 10606
18f Starkenmann C, Niclass Y, Cayeux I, Brauchli R, Gagnon A.-C. Flavour Fragrance J. 2015; 30: 91
18g Chen J, Wu J. Chin. J. Org. Chem. 2022; 42: 921

For reviews, see:

19a Dittmer DC, Hoey MD. Cyclic Sulphinic Acid Derivatives (Sultines and Sulphinamides). In The Chemistry of Sulphinic Acids, Esters and Their Derivatives. Patai S. John Wiley & Sons; Chichester: 1990. 239
19b Bondarenko OB, Saginova LG, Zyk NV. Russ. Chem. Rev. 1996; 65: 147
19c Kotha S, Khedkar P. Chem. Rev. 2012; 112: 1650

For representative examples, see:

20a Ju W, Wang X, Tian H, Gui J. J. Am. Chem. Soc. 2021; 143: 13016
20b Barbazanges M, Fensterbank L. Synlett 2018; 29: 2108
20c Jankowski P, Lindahl N, Weidow J, Wieczorek W, Johansson P. ACS Appl. Energy Mater. 2018; 1: 2582
20d Schmitt S, Bouteiller C, Barré L, Perrio C. Chem. Commun. 2011; 47: 11465
20e Xiao Y, Cui X, Martin DC. J. Electroanal. Chem. 2004; 573: 43

21 Zhang X, Ang EC. X, Yang Z, Kee CW, Tan C.-H. Nature 2022; 604: 298
22 Huang S, Zeng Z, Zhang N, Qin W, Lan Y, Yan H. Nat. Chem. 2023; 15: 185

23a Robak MT, Herbage MA, Ellman JA. Chem. Rev. 2010; 110: 3600
23b Zhou P, Chen B.-C, Davis FA. Tetrahedron 2004; 60: 8003

24a Diener HC, Peters C, Rudzio M, Noe A, Dichgans J, Haux R, Ehrmann R, Tfelt-Hansen P. J. Neurol. 1991; 238: 245
24b Deeks ED. Drugs 2011; 71: 209
24c Algethami FK. Orient. J. Chem. 2021; 37: 1077

25 Ma L, Chen S, Li G, Zhu J, Wang Q, Tang Z. ACS Catal. 2019; 9: 1525
26 Chen Y, Wu X, Yang S, Zhu C. Angew. Chem. Int. Ed. 2022; 61: e202201027