Asymmetric Synthesis of Isoxazol-5-ones and Isoxazolidin-5-ones

Antonio Macchia; Andreas Eitzinger; Jean-François Brière; Mario Waser; Antonio Massa

doi:10.1055/s-0040-1706483

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(01): 107-122
DOI: 10.1055/s-0040-1706483

short review

Asymmetric Synthesis of Isoxazol-5-ones and Isoxazolidin-5-ones

Autor*innen

Antonio Macchia

^aDepartment of Chemistry and Biology ‘A. Zambelli’, University of Salerno, Via Giovanni Paolo II, 132 84084-Fisciano (SA), Italy eMail: amassa@unisa.it
Andreas Eitzinger

^bInstitute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria eMail: mario.waser@jku.at
Jean-François Brière ∗

^cNormandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France eMail: jean-francois.briere@insa-rouen.fr
Mario Waser ∗

^bInstitute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria eMail: mario.waser@jku.at
Antonio Massa ∗

^aDepartment of Chemistry and Biology ‘A. Zambelli’, University of Salerno, Via Giovanni Paolo II, 132 84084-Fisciano (SA), Italy eMail: amassa@unisa.it

Abstract

Alle Artikel dieser Rubrik

Abstract

Isoxazol-5-ones and isoxazolidin-5-ones represent two important classes of heterocycles, with several applications as bioactive compounds and as versatile building blocks for further transformations. Unlike the parent aromatic isoxazoles, the presence of one or two stereocenters in the ring renders their asymmetric construction particularly important. In this review, starting from the description of general features and differences between these two related compound families, we present an overview on the most important enantioselective synthesis strategies to access these heterocycles. Both chiral metal catalysts and organocatalysts have recently been successfully employed for this task and some of the most promising approaches will be discussed.

1 Introduction

2 Isoxazol-5-ones as Nucleophiles

2.1 Isoxazol-5-ones as C-Nucleophiles

2.2 Isoxazol-5-ones as N-Nucleophiles

2.3 Isoxazol-5-ones as C-Nucleophiles in Cyclization Processes

3 Asymmetric Construction of Isoxazolidin-5-ones

3.1 Enantioselective α-Functionalizations of Isoxazolidin-5-ones

4 Arylideneisoxazol-5-ones in Conjugated Addition

5 Conclusions

Key words

asymmetric catalysis - organocatalysis - metal catalysts - heterocycles - chiral building blocks

Volltext

Referenzen

References
1 Lambein F, Kuo Y.-H, Van Parijs R. Heterocycles 1976; 4: 567
2 Rozan P, Kuo Y.-H, Lambein F. Phytochemistry 2001; 58: 281

3a Kuo Y.-H, Ikegami F, Lambein F. Phytochemistry 1998; 38: 32
3b Rozan P, Kuo YH, Lambein F. Amino Acids 2001; 20: 319

4a Iwama T, Nagai Y, Tamura N, Harada S, Nagaoka A. Eur. J. Pharmacol. 1991; 197: 187

See also:

4b Yu M, Wang J, Tang K, Shi X, Wang S, Zhu W.-M, Zhang X.-H. Microbiology 2012; 158: 835
4c Becker T, Pasteels J, Weigel C, Dahse H.-M, Voigt K, Boland W. Nat. Prod. Rep. 2017; 34: 343

5 Hedner E, Sjögren M, Hodzic S, Andersson R, Göransson U, Jonsson PR, Bohlin L. J. Nat. Prod. 2008; 71: 330

6a Sugeno W, Matsuda K. Appl. Entomol. Zool. 2002; 37: 191
6b Becker T, Ploss K, Boland W. Org. Biomol. Chem. 2016; 14: 6274

7a Kafle B, Aher NG, Khadka D, Park H, Cho H. Chem. Asian J. 2011; 6: 2073

See also, for antidiabetic agents:

7b Kees KL, Caggiano TJ, Steiner KE, Fitzgerald JJ. Jr, Kates MJ, Christos TE, Kulishoff JM. Jr, Moore RD, McCaleb ML. J. Med. Chem. 1995; 38: 617

8a Mahajan SS, Scian M, Sripathy S, Posakony J, Lao U, Loe TK, Leko V, Thalhofer A, Schuler AD, Bedalov A, Simon JA. J. Med. Chem. 2014; 57: 3283
8b Tong Y, Stewart KD, Thomas S, Przytulinska M, Johnson EF, Klinghofer V, Leverson J, McCall O, Soni NB, Luo Y, Lin N.-H, Sowin TJ, Giranda VL, Penning TD. Bioorg. Med. Chem. Lett. 2008; 18: 206

9 Hung TV, Janowski WK, Prager RH. Aust. J. Chem. 1985; 38: 931

10a Vergelli F, Schepetkin CI. A, Crocetti L, Iacovone A, Giovannoni MP, Guerrini G, Khlebnikov AI, Ciattini S, Ciciani G, Quinn MT. J. Enzyme Inhib. Med. Chem. 2017; 32: 821
10b Giovannoni MP, Crocetti L, Cantini N, Guerrini G, Vergelli C, Iacovone A, Teodori E, Schepetkin IA, Quinn MT, Ciattini S, Rossi P, Paoli P. Drug Dev. Res. 2020; 81: 338

11 Snyder LB, Meng Z, Mate R, Andrea SV. D, Marinier A, Quesnelle CA, Gill P, DenBleyker KL, Fung-Tomc JC, Frosco MB, Martel A, Barretta JF, Bronson JJ. Bioorg. Med. Chem. Lett. 2004; 14: 4735
12 Laufer SA, Margutti S. J. Med. Chem. 2008; 51: 2580
13 Laurent P, Braekman J.-C, Daloze D. Top. Curr. Chem. 2005; 240: 167

14a Kiyani H, Ghorbani F. Heterocycl. Lett. 2013; 3: 145
14b Conti P, Tamborini L, Pinto A, Sola L, Ettari R, Mercurio C, Micheli CD. Eur. J. Med. Chem. 2010; 45: 4331
14c Deng B.-L, Cullen MD, Zhou Z, Hartman TL, Buckheit RW. Jr, Pannecouque C, Clercq ED, Fanwick PE, Cushman M. Bioorg. Med. Chem. 2006; 14: 2366

15 Ferrazzano L, Viola A, Lonati E, Bulbarelli A, Musumeci R, Cocuzza C, Lombardo M, Tolomelli A. Eur. J. Med. Chem. 2016; 124: 906
16 Karabasanagouda T, Adhikari TA. V, Girisha M. Indian J. Chem. 2009; 48: 430
17 Dietrich H, Döller U, Gatzweiler E, Helmke H, Lehr S, Machettira A, Mcleod M, Müller T, Peters O, Rosinger C, Schmutzler D. WO 2018178008A1, 2018
18 Basak P, Dey S, Ghosh P. ChemistrySelect 2020; 5: 626
19 Becker T, Görls H, Pauls G, Wedekind R, Kai M, Boland W. J. Org. Chem. 2013; 78: 12779
20 Feng G, Satoshi I, Takuya Y, Akira U, Yukari S, Hiroshi M. Plant Sci. 2019; 283: 321

21a Lehtonen K, Summers LA, Carter GA. Pestic. Sci. 1972; 3: 357
21b Kömürcü ŞG, Rollas S, Yilmaz N, Çevikbaş A. Drug Metabol. Drug Interact. 1995; 12: 161

22 Hong S, Wei-Bing F, Feng C, De-Qing S. J. Heterocycl. Chem. 2013; 50: 1381

23a da Silva AF, Fernandes AA. G, Thurow S, Stivanin ML, Jurberg ID. Synthesis 2018; 50: 2473
23b Fernandes AA. G, da Silva AF, Thurow S, Okada CY. Jr, Jurberg ID. Targets Heterocycl. Syst. 2018; 22: 409

24 Review: Zard SZ. Chem. Commun. 2002; 1555

25a Abidi SL. J. Chem. Soc., Chem. Commun. 1985; 1222
25b Abidi SL. Tetrahedron Lett. 1986; 27: 267
25c Abidi SL. J. Org. Chem. 1986; 51: 2687
25d Corey EJ, Seibel WL, Kappos JC. Tetrahedron Lett. 1987; 28: 4921
25e Boivin J, Elkaim L, Ferro PG, Zard SZ. Tetrahedron Lett. 1991; 32: 5321

26 Annibaletto J, Oudeyer S, Levacher V, Brière J.-F. Synthesis 2017; 49: 2117
27 Benson SW. J. Chem. Educ. 1965; 42: 502

28a Baldwin JE, Harwood LM, Lombard MJ. Tetrahedron 1984; 40: 4363
28b Baldwin JE, Adlington RM, Mellor LC. Tetrahedron 1994; 50: 5049
28c Pearson C, Rinehart KL, Sugano M, Costerison JR. Org. Lett. 2000; 2: 2901
28d Lee H.-S, Park J.-S, Kim BM, Gellman SH. J. Org. Chem. 2003; 68: 1575

29 Rieckhoff S, Meisner J, Kästner J, Frey W, Peters R. Angew. Chem. Int. Ed. 2018; 57: 1404
30 Meng W.-T, Zheng Y, Nie J, Xiong H.-Y, Ma J.-A. J. Org. Chem. 2013; 78: 559
31 Zhang H, Wang B, Cui L, Bao X, Qu J, Song Y. Eur. J. Org. Chem. 2015; 2143
32 Hellmuth T, Frey W, Peters R. Angew. Chem. Int. Ed. 2015; 54: 2788
33 Torán R, Vila C, Sanz-Marco A, Muñoz MC, Pedro JR, Blay G. Eur. J. Org. Chem. 2020; 627
34 Qi S.-S, Jiang Z.-H, Chu M.-M, Wang Y.-F, Chen X.-Y, Ju W.-Z, Xu D.-Q. Org. Biomol. Chem. 2020; 18: 2398
35 Xiao W, Zhou Z, Yang Q.-Q, Du W, Chen Y.-C. Adv. Synth. Catal. 2018; 360: 3526
36 Li L, Luo P, Deng Y, Shao Z. Angew. Chem. Int. Ed. 2019; 58: 4710

37a Baldwin SW, Aubé J. Tetrahedron Lett. 1987; 28: 179
37b Ishikawa T, Nagai K, Kudoh T, Saito S. Synlett 1995; 1171
37c Niu D, Zhao K. J. Am. Chem. Soc. 1999; 121: 2456

38a Sibi MP, Liu M. Org. Lett. 2000; 2: 3393
38b Sibi MP, Prabagaran N, Ghorpade SG, Jasperse CP. J. Am. Chem. Soc. 2003; 125: 11796

39 Izumi S, Kobayashi Y, Takemoto Y. Org. Lett. 2016; 18: 696
40 Berini C, Sebban M, Oulyadi H, Sanselme M, Levacher V, Brière J.-F. Org. Lett. 2015; 17: 5408

41a Ibrahem I, Rios R, Vesely J, Zhao G.-L, Córdova A. Chem. Commun. 2007; 849
41b Pou A, Moyano A. Eur. J. Org. Chem. 2013; 3103
41c Jiang H.-T, Gao H.-L, Ge C.-S. Chin. Chem. Lett. 2017; 28: 471
41d Lai J, Sayalero S, Ferrali A, Osorio-Planes L, Bravo F, Rodríguez-Escrich C, Pericàs MA. Adv. Synth. Catal. 2018; 360: 2914
41e Gao H, Yu J, Ge C, Jiang Q. Molecules 2018; 23: 1440

42 Zhang H, Zhang S.-J, Zhou Q, Dong L, Chen Y.-C. Beilstein J. Org. Chem. 2012; 8: 1241
43 Kamlar M, Císařová I, Hybelbauerová S, Veselý J. Eur. J. Org. Chem. 2017; 1926
44 Martzel T, Annibaletto J, Millet P, Pair E, Sanselme M, Oudeyer S, Levacher V, Brière J.-F. Chem. Eur. J. 2020; 26: 8541
45 Pair E, Cadart T, Levacher V, Brière J.-F. ChemCatChem 2016; 8: 1882

46a Seayad J, Patra PK, Zhang Y, Ying JY. Org. Lett. 2008; 10: 953
46b Nawaz F, Zaghouani M, Bonne D, Chuzel O, Rodriguez J, Coquerel Y. Eur. J. Org. Chem. 2013; 8253

47 Ji S.-P, Liu L.-W, Chen F, Ren H.-X, Yang Y, Zhang Z.-B, Peng L, Wang L.-X. Eur. J. Org. Chem. 2016; 5437

48a Shindo M, Itoh K, Ohtsuki K, Tsuchiya C, Shishido K. Synthesis 2003; 1441
48b Luisi R, Capriati V, Florio S, Vista T. J. Org. Chem. 2013; 68: 9861

49a Postikova S, Tite T, Levacher V, Brière J.-F. Adv. Synth. Catal. 2013; 355: 2513
49b Tite T, Sabbah M, Levacher V, Brière J.-F. Chem. Commun. 2013; 49: 11569

50 Cadart T, Berthonneau C, Levacher V, Perrio S, Brière J.-F. Chem. Eur. J. 2016; 22: 15261

51a Cadart T, Levacher V, Perrio S, Brière J.-F. Adv. Synth. Catal. 2018; 360: 1499
51b Capaccio V, Zielke K, Eitzinger A, Massa A, Palombi L, Faust K, Waser M. Org. Chem. Front. 2018; 5: 3336
51c Eitzinger A, Winter M, Schörgenhumer J, Waser M. Chem. Commun. 2020; 56: 579

52a Capaccio V, Sicignano M, Rodriguez RI, Della Sala G, Aleman J. Org. Lett. 2020; 22: 219
52b Eitzinger A, Brière J.-F, Cahard D, Waser M. Org. Biomol. Chem. 2020; 18: 405

53a Yu J.-S, Noda H, Shibasaki M. Angew. Chem. Int. Ed. 2018; 57: 818
53b De Oliveira MN, Arseniyadis S, Cossy J. Chem. Eur. J. 2018; 24: 4810

54a Yu J.-S, Noda H, Shibasaki M. Chem. Eur. J. 2018; 24: 15796
54b Amemiya F, Noda H, Shibasaki M. Chem. Pharm. Bull. 2019; 67: 1046

55a Yu J.-S, Espinosa M, Noda H, Shibasaki M. J. Am. Chem. Soc. 2019; 141: 10530
55b Espinosa M, Noda H, Shibasaki M. Org. Lett. 2019; 21: 9296

56 Seminal report about the use of such catalysts: Ooi T, Kameda M, Maruoka K. J. Am. Chem. Soc. 1999; 121: 6519

For some illustrative overviews:

57a Shirakawa S, Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312
57b Qia D, Sun J. Chem. Eur. J. 2019; 25: 3740
57c Nakamura T, Okuno K, Nishiyori R, Shirakawa S. Chem. Asian J. 2020; 15: 463

58a Bode JW. M, Fox RM, Baucom KD. Angew. Chem. Int. Ed. 2006; 45: 1248
58b Wucherpfennig TG, Pattabiraman VR, Limberg FR. P, Ruiz-Rodriguez J, Bode JW. Angew. Chem. Int. Ed. 2014; 53: 12248

59 Cui B.-D, Li S.-W, Zuo J, Wu Z.-J, Zhang X.-M, Yuan W.-C. Tetrahedron 2014; 70: 1895
60 Macchia A, Cuomo VD, Di Mola A, Pierri G, Tedesco C, Palombi L, Massa A. Eur. J. Org. Chem. 2020; 2264
61 Jurberg ID. Chem. Eur. J. 2017; 23: 9716
62 Parveen M, Aslam A, Ahmad A, Alam M, Silva MR, Silva PS. P. J. Mol. Struct. 2020; 1200: 127067
63 Martínez-Pardo P, Laviós A, Sanz-Marco A, Vila C, Pedro JR, Blay G. Adv. Synth. Catal. 2020; 362: 3564
64 Xiao W, Yang Q.-Q, Chen Z, Ouyang Q, Du W, Chen Y.-C. Org. Lett. 2018; 20: 236
65 Feng X, Zhou Z, Zhou R, Zhou Q.-Q, Dong L, Chen Y.-C. J. Am. Chem. Soc. 2012; 134: 19942
66 Ye Z, Bai L, Bai Y, Gan Z, Zhou H, Pan T, Yu Y, Zhou J. Tetrahedron 2019; 75: 682
67 Massa A, Roscigno A, De Caprariis P, Filosa R, Di Mola A. Adv. Synth. Catal. 2010; 352: 3348
68 More V, Di Mola A, Perillo M, De Caprariis P, Filosa R, Peduto A, Massa A. Synthesis 2011; 3027
69 Di Mola A, Di Martino M, Capaccio V, Pierri G, Palombi L, Tedesco C, Massa A. Eur. J. Org. Chem. 2018; 1699
70 Di Mola A, Macchia A, Tedesco C, Pierri G, Palombi L, Filosa R, Massa A. ChemistrySelect 2019; 4: 4820