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CC BY 4.0 · SynOpen 2025; 09(04): 214-235
DOI: 10.1055/a-2713-6067
DOI: 10.1055/a-2713-6067
graphical review
Approaches to the Construction of Endocyclic Sulfoximines
Autoren
This work is dedicated to individuals and organizations supporting Ukrainian chemists
Abstract
Endocyclic sulfoximines are a relatively novel class of cyclic sulfoximines where the S(O)=N group is a part of a ring structure. They possess unique physicochemical and structural features, including three-dimensionality and chirality, amid chemical and thermal stability. This graphical review presents a comprehensive compilation of synthetic approaches toward endocyclic sulfoximines, organized by the type of reaction employed. The reaction conditions are presented in a detailed manner; the proposed reaction mechanisms and the catalytic cycles are also provided.
Publikationsverlauf
Eingereicht: 25. August 2025
Angenommen nach Revision: 29. September 2025
Accepted Manuscript online:
29. September 2025
Artikel online veröffentlicht:
29. Oktober 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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References
- 2a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
- 2b Lovering F. Med. Chem. Commun. 2013; 4: 515
- 3 Boulard E, Zibulski V, Oertel L, Lienau P, Schäfer M, Ganzer U, Lücking U. Chem. Eur. J. 2020; 26: 4378
- 4a Han Z, Reeves DC, Krishnamurthy D, Senanayake CH. In Comprehensive Chirality, Vol. 3. Yamamoto H. Elsevier; Amsterdam: 2012: 560
- 4b Andresini M, Tota A, Degennaro L, Bull JA, Luisi R. Chem. Eur. J. 2021; 27: 17293
- 4c Shultz ZP, Lopchuk JM. Strategies for the Synthesis of Sulfoximine-Containing Heterocycles . In Advances in Heterocyclic Chemistry, Vol. 138. Scriven EF. V, Ramsden CA. Academic Press; Cambridge: 2022: 61
- 4d Luisi R, Bull JA. Molecules 2023; 28: 1120
- 4e Wang B, Liang X, Zeng Q. Molecules 2023; 28: 1367
- 4f Zeng Q, Nking’wa AA. Sulfoximines . Springer Nature; Singapore: 2025
- 4g Mäder P, Kattner L. J. Med. Chem. 2020; 63: 14243
- 4h Han Y, Xing K, Zhang J, Tong T, Shi Y, Cao H, Yu H, Zhang Y, Liu D, Zhao L. Eur. J. Med. Chem. 2021; 209: 112885
- 4i Lücking U. Chem. Eur. J. 2022; 28: e202201993
- 5a Johnson CR, Katekar GF, Huxol RF, Janiga ER. J. Am. Chem. Soc. 1971; 93: 3771
- 5b Johnson CR, Janiga ER. J. Am. Chem. Soc. 1973; 95: 7692
- 5c Boßhammer S. Synthesis 1998; 919
- 5d Baldon S, Paut J, Anselmi E, Dagousset G, Tuccio B, Pelosi G, Cuadros S, Magnier E, Dell’Amico L. Chem. Sci. 2025; 16: 6957
- 6a Wang H, Frings M, Bolm C. Org. Lett. 2016; 18: 2431
- 6b Yang J, Gao W, Teng Y, Yu L, Huang K, Li Q, Xie H, Li T. Eur. J. Org. Chem. 2024; 27: e202300927
- 7a Harmata M, Schlemper EO. Tetrahedron Lett. 1987; 28: 5997
- 7b Harmata M, Claassen RJ, Barnes CL. J. Org. Chem. 1991; 56: 5059
- 7c Harmata M, Jones DE. Tetrahedron Lett. 1995; 36: 4769
- 7d Harmata M, Kahraman M, Jones DE, Pavri N, Weatherwax SE. Tetrahedron 1998; 54: 9995
- 7e Harmata M, Kahraman M. J. Org. Chem. 1998; 63: 6845
- 8a Harmata M, Pavri N. Angew. Chem. Int. Ed. 1999; 38: 2419
- 8b Battula SR. K, Subbareddy GV, Chakravarthy IE, Saravanan V. RSC Adv. 2016; 6: 55710
- 9a Williams TR, Cram DJ. J. Am. Chem. Soc. 1971; 93: 7333
- 9b Williams TR, Cram DJ. J. Org. Chem. 1973; 38: 20
- 9c Barnes AC, Kennewell PD, Taylor JB. J. Chem. Soc., Chem. Commun. 1973; 776
- 9d Le T.-N, Diter P, Pégot B, Bournaud C, Toffano M, Guillot R, Vo-Thanh G, Magnier E. Org. Lett. 2016; 18: 5102
- 9e Schaffner-Sabba K, Tomaselli H, Henrici B, Renfroe HB. J. Org. Chem. 1977; 42: 952
- 10a Ried W, Saynovits M. Chem. Ber. 1988; 121: 1005
- 10b Furukawa S, Watanabe M, Minohara M, Masuda K, Kinoshita T. Heterocycles 1976; 4: 1875
- 10c Bonacorso H, Vezzosi R, Drekener R, Zanatta N, Martins M. Lett. Org. Chem. 2009; 6: 145
- 10d Tamura Y, Tsunekawa M, Miyamoto T, Ikeda M. J. Org. Chem. 1977; 42: 602
- 11a Chuchvera YO, Korobka OP, Horbatochkin YO, Ostapchuk EN, Popova MV, Shishkina SV, Volovenko YM, Dobrydnev AV. Synlett 2025; 36: 2876
- 11b Milokhov DS, Pomalin MS, Lutsiuk TM, Hys VY, Virych PA, Poliudov AO, Popova M, Shishkina S, Volovenko YM, Dobrydnev AV. Synlett 2025; 36: 2615
- 12a Marco JL, Ingate ST, Chinchón PM. Tetrahedron 1999; 55: 7625
- 12b Marco JL, Ingate ST, Jaime C, Beá I. Tetrahedron 2000; 56: 2523
- 12c Postel D, Van Nhien AN, Marco JL. Eur. J. Org. Chem. 2003; 3713
- 12d Dobrydnev AV, Marco Contelles J. Eur. J. Org. Chem. 2021; 1229
- 13 Hua Y, Zhang W, Wang X, Ge Z, Li R. Tetrahedron 2017; 73: 4387
- 14 Stoss P, Satzinger G. Angew. Chem. Int. Ed. 1971; 10: 76
- 15 Marzag H, Schuler M, Tatibouët A, Reboul V. Eur. J. Org. Chem. 2017; 896
- 16a Ma Y.-N, Guo C.-Y, Zhao Q, Zhang J, Chen X. Green Chem. 2018; 20: 2953
- 16b Ma Y.-N, Bian Y, Liu X, Zhang J, Chen X. J. Org. Chem. 2019; 84: 450
- 16c Li L, Li Y, Zhao Z, Luo H, Ma Y.-N. Org. Lett. 2019; 21: 5995
- 16d Ma Y.-N, Gao Y, Jing Y, Kang J, Zhang J, Chen X. J. Org. Chem. 2020; 85: 2918
- 17a Bolm C, Villar H. Synthesis 2005; 1421
- 17b Barthelemy A, Prieto A, Diter P, Hannedouche J, Toffano M, Anselmi E, Magnier E. Eur. J. Org. Chem. 2018; 3764
- 17c Füger B, Bolm C. Synlett 2009; 1601
- 18a Bolm C, Martin M, Gibson L. Synlett 2002; 832
- 18b Bolm C, Okamura H, Verrucci M. J. Organomet. Chem. 2003; 687: 444
- 18c Ren Y, Mo L, Wang Y, Yu L, Yin M, Xiong Z, Teng F, He Y. J. Org. Chem. 2024; 89: 3345
- 19a Harmata M, Rayanil K, Gomes MG, Zheng P, Calkins NL, Kim S.-Y, Fan Y, Bumbu V, Lee DR, Wacharasindhu S, Hong X. Org. Lett. 2005; 7: 143
- 19b Dong W, Wang L, Parthasarathy K, Pan F, Bolm C. Angew. Chem. Int. Ed. 2013; 52: 11573
- 19c Liu Y, Hu Y, Lv G, Nie R, Peng Y, Zhang C, Lv S, Hai L, Wang H, Wu Y. ACS Sustainable Chem. Eng. 2019; 7: 13425
- 19d Hanchate V, Muniraj N, Prabhu KR. J. Org. Chem. 2019; 84: 8248
- 19e Hanchate V, Kumar A, Prabhu KR. J. Org. Chem. 2019; 84: 11335
- 20a Li S, Liu L, Wang R, Yang Y, Li J, Wei J. Org. Lett. 2020; 22: 7470
- 20b Garimallaprabhakaran A, Hong X, Harmata M. ARKIVOC 2012; (vi): 119
- 21a Zhou T, Qian P.-F, Li J.-Y, Zhou Y.-B, Li H.-C, Chen H.-Y, Shi B.-F. J. Am. Chem. Soc. 2021; 143: 6810
- 21b Huang L.-T, Hirata Y, Kato Y, Lin L, Kojima M, Yoshino T, Matsunaga S. Synthesis 2022; 54: 4703
- 21c Zheng G, Tian M, Xu Y, Chen X, Li X. Org. Chem. Front. 2018; 5: 998
- 22a Cheng Y, Bolm C. Angew. Chem. Int. Ed. 2015; 54: 12349
- 22b Sun Y, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 15539
- 22c Shen B, Wan B, Li X. Angew. Chem. Int. Ed. 2018; 57: 15534
- 22d Li J.-Y, Xie P.-P, Zhou T, Qian P.-F, Zhou Y.-B, Li H.-C, Hong X, Shi B.-F. ACS Catal. 2022; 12: 9083
- 22e Li J, Li H, Fang D, Liu L, Han X, Sun J, Li C, Zhou Y, Ye D, Liu H. J. Org. Chem. 2021; 86: 15217
- 22f Ko GH, Son J, Kim H, Maeng C, Baek Y, Seo B, Um K, Lee PH. Adv. Synth. Catal. 2017; 359: 3362
- 22g Wang B, Han X, Li J, Li C, Liu H. Molecules 2020; 25: 2515
- 22h Jeon WH, Son J.-Y, Kim JE, Lee PH. Org. Lett. 2016; 18: 3498
- 23 Yu H, Li Z, Bolm C. Angew. Chem. Int. Ed. 2018; 57: 12053
- 24a Shi P, Tu Y, Wang C, Kong D, Ma D, Bolm C. Org. Lett. 2020; 22: 8842
- 24b Huang J, Huang Y, Wang T, Huang Q, Wang Z, Chen Z. Org. Lett. 2017; 19: 1128
- 24c Hirata Y, Sekine D, Kato Y, Lin L, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2022; 61: e202205341
- 24d Xu H.-B, Yang J.-H, Chai X.-Y, Zhu Y.-Y, Dong L. Org. Lett. 2020; 22: 2060
- 25a Huang G, Shan Y, Yu J.-T, Pan C. Org. Biomol. Chem. 2021; 19: 10085
- 25b Chen L, Wang Z, Wang Y, Hao L, Xu X, Wu G, Ji Y. Org. Biomol. Chem. 2022; 20: 887
- 26 Qian P.-F, Zhou T, Li J.-Y, Zhou Y.-B, Shi B.-F. ACS Catal. 2022; 12: 13876
- 27a Ye W, Zhang L, Ni C, Rong J, Hu J. Chem. Commun. 2014; 50: 10596
- 27b Rong J, Ni C, Gu Y, Hu J. Helv. Chim. Acta 2021; 104: e2100019
- 28a Aota Y, Maeda Y, Kano T, Maruoka K. Chem. Eur. J. 2019; 25: 15755
- 28b Cividino P, Verrier C, Philouze C, Carret S, Poisson J. Adv. Synth. Catal. 2019; 361: 1236
- 28c Barthelemy A.-L, Anselmi E, Le T.-N, Vo-Thanh G, Guillot R, Miqueu K, Magnier E. J. Org. Chem. 2019; 84: 4086
- 29 Moragas T, Liffey RM, Regentová D, Ward JS, Dutton J, Lewis W, Churcher I, Walton L, Souto JA, Stockman RA. Angew. Chem. Int. Ed. 2016; 55: 10047