Inter- and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes

Shoko Yamazaki; Zhichao Wang; Kentaro Iwata; Khotaro Katayama; Hirotaka Sugiura; Yuji Mikata; Tsumoru Morimoto; Akiya Ogawa

doi:10.1055/s-0040-1706547

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(04): 731-753
DOI: 10.1055/s-0040-1706547

paper

Inter- and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes

Shoko Yamazaki∗

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan eMail: yamazaks@cc.nara-edu.ac.jp

,

Zhichao Wang

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan

,

Kentaro Iwata

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan eMail: yamazaks@cc.nara-edu.ac.jp

,

Khotaro Katayama

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan eMail: yamazaks@cc.nara-edu.ac.jp

,

Hirotaka Sugiura

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan

,

Yuji Mikata

^cKYOUSEI Science Center, Nara Women’s University, Nara 630-8506, Japan

,

Tsumoru Morimoto

^dGraduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan

,

Akiya Ogawa

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Inter- and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl₄ or SnBr₄ stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides, including in situ generated derivatives, showed high diversity of reaction modes depending on the structures and substituents of the substrates. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were discussed based on the DFT calculations.

Key words

cyclobutane - ethenetricarboxylate - styrene - intermolecular cycloaddition - intramolecular cycloaddition

Volltext

Referenzen

References

1a Dembitsky VM. J. Nat. Med. 2008; 62: 1
1b Dembitsky VM. Phytomedicine 2014; 21: 1559
1c Gutekunst WR, Baran PS. J. Org. Chem. 2014; 79: 2430
1d Beniddir MA, Joseph LD, Skiredj A, Poupon E. Nat. Prod. Rep. 2016; 33: 820
1e Li J, Gao K, Bian M, Ding H. Org. Chem. Front. 2020; 7: 136

2a Chen S, Shan G, Nie P, Rao Y. Asian J. Org. Chem. 2015; 4: 16
2b Namyslo JC, Kaufmann DE. Chem. Rev. 2003; 103: 1485
2c Lee-Ruff E, Mladenova G. Chem. Rev. 2003; 103: 1449
2d Matsuo J. Tetrahedron Lett. 2014; 55: 2589

3a Poplata S, Tröster A, Zou Y.-Q, Bach T. Chem. Rev. 2016; 116: 9748
3b Yoon TP. ACS Catal. 2013; 3: 895
3c Yoon TP. Acc. Chem. Res. 2016; 49: 2307

4a Kriis K, Ausmees K, Pehk T, Lopp M, Kanger T. Org. Lett. 2010; 12: 2230
4b Ausmees K, Kriis K, Pehk T, Werner F, Järving I, Lopp M, Kanger T. J. Org. Chem. 2012; 77: 10680
4c Reinart-Okugbeni R, Ausmees K, Kriis K, Werner F, Rinken A, Kanger T. Eur. J. Med. Chem. 2012; 55: 255
4d Araki T, Ozawa T, Yokoe H, Kanematsu M, Yoshida M, Shishido K. Org. Lett. 2013; 15: 200
4e Hoshikawa T, Tanji K, Matsuo J, Ishibashi H. Chem. Pharm. Bull. 2012; 60: 548
4f Padwa A, Lipka H, Watterson SH, Murphree SS. J. Org. Chem. 2003; 68: 6238
4g Brummond KM, Chen D. Org. Lett. 2005; 7: 3473
4h Ovaska TV, Kyne RE. Tetrahedron Lett. 2008; 49: 376

5 Huisgen R. Acc. Chem. Res. 1977; 10: 117

6a Hu J.-L, Feng L.-W, Wang L, Xie Z, Tang Y, Li X. J. Am. Chem. Soc. 2016; 138: 13151
6b Parsons AT, Johnson JS. J. Am. Chem. Soc. 2009; 131: 14202
6c Baar MR, Ballesteros P, Roberts BW. Tetrahedron Lett. 1986; 27: 2083
6d Yamazaki S, Tanaka M, Inoue T, Morimoto N, Kumagai H, Yamamoto K. J. Org. Chem. 1995; 60: 6546
6e De-Nanteuil F, Waser J. Angew. Chem. Int. Ed. 2013; 52: 9009

7a De Keyser J.-L, De Cock CJ. C, Poupaert JH, Dumont P. J. Org. Chem. 1988; 53: 4859
7b Ballesteros P, Roberts BW. Org. Synth. Coll. Vol. 7 1990; 142

8a Yamazaki S, Yamamoto Y, Fukushima Y, Takebayashi M, Ukai T, Mikata Y. J. Org. Chem. 2010; 75: 5216
8b Yamazaki S, Takebayashi M, Miyazaki K. J. Org. Chem. 2010; 75: 1188
8c Yamazaki S, Iwata Y, Fukushima Y. Org. Biomol. Chem. 2009; 7: 655
8d Morikawa S, Yamazaki S, Tsukada M, Izuhara S, Morimoto T, Kakiuchi K. J. Org. Chem. 2007; 72: 6459
8e Yamazaki S, Iwata Y. J. Org. Chem. 2006; 71: 739
8f Yamazaki S, Ueda K, Fukushima Y, Ogawa A, Kakiuchi K. Eur. J. Org. Chem. 2014; 7023
8g Yamazaki S, Maenaka Y, Fujinami K, Mikata Y. RSC Adv. 2012; 2: 8095

9a Srisiri W, Padias AB, Hall HK. Jr. J. Org. Chem. 1994; 59: 5424
9b Engler TA, Combrink KD, Letavic MA, Lynch KO. Jr, Ray JE. J. Org. Chem. 1994; 59: 6567
9c Murphy WS, Neville D. Tetrahedron Lett. 1996; 37: 9397
9d Wang L, Lv J, Li S, Luo S. Org. Lett. 2017; 19: 3366

10a Okamoto K, Tamura E, Ohe K. Angew. Chem. Int. Ed. 2013; 52: 10639
10b Qin Y, Lv J, Luo S, Cheng J.-P. Org. Lett. 2014; 16: 5032

11a Hsu D.-S, Huang J.-Y. J. Org. Chem. 2012; 77: 2659
11b Manning WB. Tetrahedron Lett. 1979; 20: 1661
11c Zheng M, Wu F, Chen K, Zhu S. Org. Lett. 2016; 18: 3554
11d Diment A, Ritchie E, Taylor WC. Aust. J. Chem. 1969; 22: 1721
11e Stranix BR, Darling GD. J. Org. Chem. 1997; 62: 9001
11f Carreño MC, Mahugo J, Urbano A. Tetrahedron Lett. 1997; 38: 3047
11g Bhojgude SS, Bhunia A, Gonnade RG, Biju AT. Org. Lett. 2014; 16: 676
11h Kolis SP, Chordia MD, Liu R, Kopach ME, Harman WD. J. Am. Chem. Soc. 1998; 120: 2218
11i Parker KA, Ruder SM. J. Am. Chem. Soc. 1989; 111: 5948
11j Newman MS, Dhawan B, Hashem MM, Khanna VK, Springer JM. J. Org. Chem. 1976; 41: 3925

12 Snider BB, Roush DM. J. Org. Chem. 1979; 44: 4229

13a Yamazaki S, Sugiura H, Ohashi S, Ishizuka K, Saimu R, Mikata Y, Ogawa A. J. Org. Chem. 2016; 81: 10863
13b Sugiura H, Yamazaki S, Go K, Ogawa A. Eur. J. Org. Chem. 2019; 204

14 Seechurn CC. C. J, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
15 Chan PW. H, Kamijo S, Yamamoto Y. Synlett 2001; 910

16a Holt C, Alachouzos G, Frontier AJ. J. Am. Chem. Soc. 2019; 141: 5461
16b Alachouzos G, Frontier AJ. J. Am. Chem. Soc. 2019; 141: 118
16c Alachouzos G, Frontier AJ. Angew. Chem. Int. Ed. 2017; 56: 15030
16d Zhou X, Zhang H, Xie X, Li Y. J. Org. Chem. 2008; 73: 3958

17 Schubert WM, Barfknecht GW. J. Am. Chem. Soc. 1970; 92: 207

18a Ko C, Feltenberger JB, Ghosh SK, Hsung RP. Org. Lett. 2008; 10: 1971
18b Nakano S, Kakugawa K, Nemoto T, Hamada Y. Adv. Synth. Catal. 2014; 356: 2088
18c Luzung MR, Mauleón P, Toste FD. J. Am. Chem. Soc. 2007; 129: 12402
18d Ranieri B, Obradors C, Mato M, Echavarren AM. Org. Lett. 2016; 18: 1614
18e Gulías M, Collado A, Trillo B, López F, Oñate E, Esteruelas MA, Mascareñas JL. J. Am. Chem. Soc. 2011; 133: 7660
18f Zhao J.-F, Loh T.-P. Angew. Chem. Int. Ed. 2009; 48: 7232

19a Sternbach DD, Rossana DM. Tetrahedron Lett. 1982; 23: 303
19b Jung ME, Street LJ. J. Am. Chem. Soc. 1984; 106: 8327
19c Sternbach DD, Rossana DM, Onan KD. Tetrahedron Lett. 1985; 26: 591
19d Jung ME. Synlett 1990; 186
19e Jung ME, Gervay J. Tetrahedron Lett. 1990; 31: 4685
19f Jung ME, Gervay J. J. Am. Chem. Soc. 1991; 113: 224
19g Hudlicky T, Butora G, Fearnley SP, Gum AG, Persichini PJ. III, Stabile MR, Merola JS. J. Chem. Soc., Perkin Trans. 1 1995; 2393
19h Giessner-Prettre C, Hückel S, Maddaluno J, Jung ME. J. Org. Chem. 1997; 62: 1439
19i Jung ME, Kiankarimi M. J. Org. Chem. 1998; 63: 2968
19j Schwan AL, Snelgrove JL, Kalin ML, Froese RD. J, Morokuma K. Org. Lett. 1999; 1: 487
19k Jung ME, Min S.-J. J. Am. Chem. Soc. 2005; 127: 10834
19l Padwa A, Wang Q. J. Org. Chem. 2006; 71: 3210
19m Paulvannan K, Jacobs JW. Tetrahedron 1999; 55: 7433

20a Townsend SD, Ross AG, Liu K, Danishefsky SJ. Proc. Natl. Acad. Sci. U.S.A. 2014; 111: 7931
20b Meinwald J, Tufariello JJ, Hurst JJ. J. Org. Chem. 1964; 29: 2914
20c Corey EJ, Bass JD, LeMahieu R, Mitra RB. J. Am. Chem. Soc. 1964; 86: 5570
20d Wiberg KB, Hiatt JE, Hseih K. J. Am. Chem. Soc. 1970; 92: 544
20e Wiberg KB, Pfeiffer JG. J. Am. Chem. Soc. 1970; 92: 553

21 Oppolzer W, Achini R, Pfenninger E, Weber HP. Helv. Chim. Acta 1976; 59: 1186
22 The structure of the byproduct 34 was deduced from the spectra and our previous result: Yamazaki S, Fujinami K, Maitoko Y, Ueda K, Kakiuchi K. J. Org. Chem. 2013; 78: 8405

23a Becke AD. J. Chem. Phys. 1993; 98: 5648
23b Lee C, Yang W, Parr RG. Phys. Rev. B 1998; 37: 785

24 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01. Gaussian, Inc; Wallingford CT: 2009

25a Cancès E, Mennucci B, Tomasi J. J. Chem. Phys. 1997; 107: 3032
25b Cossi M, Barone V, Mennucci B, Tomasi J. Chem. Phys. Lett. 1998; 286: 253
25c Mennucci B, Tomasi J. J. Chem. Phys. 1997; 106: 5151

26a Fukui K. J. Phys. Chem. 1970; 74: 4161
26b Gonzalez C, Schlegel HB. J. Phys. Chem. 1989; 90: 2154

27 Yamazaki S, Ohmitsu K, Ohi K, Otsubo T, Moriyama K. Org. Lett. 2005; 7: 759
28 Barluenga J, Fañanás FJ, Sanz R, Marcos C, Ignacio JM. Chem. Commun. 2005; 933
29 Saputra MA, Ngo L, Kartika R. J. Org. Chem. 2015; 80: 8815
30 Sato AH, Mihara S, Iwasawa T. Tetrahedron Lett. 2012; 53: 3585
31 Suga H, Hamatani T, Guggisberg Y, Schlosser M. Tetrahedron 1990; 46: 4255

32a Olsen DK, Torian BE, Morgan CD, Braun LL. J. Org. Chem. 1980; 45: 4049
32b Schlummer B, Hartwig JF. Org. Lett. 2002; 4: 1471

33 Ravinder B, Rajeswar RS, Panasa RA, Rakeshwar B. Tetrahedron Lett. 2013; 54: 4908

Zusatzmaterial

Supporting Information