Fernández, I. & Khiar, N. Recent developments in the synthesis and utilization of chiral sulfoxides. Chem. Rev. 103, 3651–3706 (2003).
Robak, M. T., Herbage, M. A. & Ellman, J. A. Synthesis and applications of tert-butanesulfinamide. Chem. Rev. 110, 3600–3740 (2010).
Lücking, U. Sulfoximines: A neglected opportunity in medicinal chemistry. Angew. Chem. Int. Ed. 52, 9399–9408 (2013).
Bizet, V., Kowalczyk, R. & Bolm, C. Fluorinated sulfoximines: Syntheses, properties and applications. Chem. Soc. Rev. 43, 2426–2438 (2014).
Shen, X. & Hu, J. Fluorinated sulfoximines: Preparation, reactions and applications. Eur. J. Org. Chem. 2014, 4437–4451 (2014).
Frings, M., Bolm, C., Blum, A. & Gnamm, C. Sulfoximines from a medicinal chemist’s perspective: Physicochemical and in vitro parameters relevant for drug discovery. Eur. J. Med. Chem. 126, 225–245 (2017).
Wiezorek, S., Lamers, P. & Bolm, C. Conversion and degradation pathways of sulfoximines. Chem. Soc. Rev. 48, 5408–5423 (2019).
Passia, M. T., Schöbel, J.-H. & Bolm, C. Sulfondiimines: Synthesis, derivatisation and application. Chem. Soc. Rev. 51, 4890–4901 (2022).
Tilby, M. J., Dewez, D. F., Hall, A., Martínez Lamenca, C. & Willis, M. C. Exploiting configurational lability in Aza-sulfur compounds for the organocatalytic enantioselective synthesis of sulfonimidamides. Angew. Chem. Int. Ed. 60, 25680–25687 (2021).
Wojaczyńska, E. & Wojaczyński, J. Enantioselective synthesis of sulfoxides: 2000−2009. Chem. Rev. 110, 4303–4356 (2010).
Han, J., Soloshonok, V. A., Klika, K. D., Drabowicz, J. & Wzorek, A. Chiral sulfoxides: advances in asymmetric synthesis and problems with the accurate determination of the stereochemical outcome. Chem. Soc. Rev. 47, 1307–1350 (2018).
Zhang, X., Wang, F. & Tan, C.-H. Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers. JACS Au 3, 700–714 (2023).
Suleman, M., Huang, T., Zhou, T., Chen, Z. & Shi, B. Recent advances in asymmetric synthesis of chiral-at-sulfur sulfoximines. ACS Catal. 15, 5511–5530 (2025).
Yang, J. et al. Catalytic enantioselective reductive arylation and alkenylation of sulfinylamines to access sulfinamides enabled by cobalt catalysis. Angew. Chem. Int. Ed. 64, e202506243 (2025).
Tsuzuki, S. & Kano, T. Asymmetric synthesis of chiral sulfimides through the O-alkylation of enantioenriched sulfinamides and addition of carbon nucleophiles. Angew. Chem. Int. Ed. 62, e202300637 (2023).
Jiang, X. et al. Engineering of methionine sulfoxide reductase A with expanded substrate scope for deracemization of sulfinyl esters. ACS Sustain. Chem. Eng. 12, 11987–11996 (2024).
Xi, L., Fang, X., Wang, M. & Shi, Z. Asymmetric 2,3-addition of sulfinylamines with arylboronic acids enabled by nickel catalysis. J. Am. Chem. Soc. 146, 17587–17594 (2024).
Shi, Y., Yuan, Y., Li, J., Yang, J. & Zhang, J. Catalytic asymmetric synthesis of sulfinamides via Cu-catalyzed asymmetric addition of aryl boroxines to sulfinylamines. J. Am. Chem. Soc. 146, 17580–17586 (2024).
Fang, X. et al. Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides. Nat. Commun. 16, 377 (2025).
Jiang, H.-J. et al. Unlocking chiral sulfinimidoyl electrophiles: Asymmetric synthesis of sulfinamides catalyzed by anionic stereogenic-at-cobalt(III) complexes. J. Am. Chem. Soc. 147, 2137–2147 (2025).
Andersen, K. K. Synthesis of (+)-ethyl p-tolyl sulfoxide from (−)-menthyl (−)-p-toluenrsulfinate. Tetrahedron Lett. 3, 93–95 (1962).
Wudl, F. & Lee, T. B. K. Novel asymmetric synthesis of chiral sulphoxides. J. Chem. Soc., Chem. Commun. 61–62 (1972).
Rebiere, F., Samuel, O., Ricard, L. & Kagan, H. B. A general route to enantiomerically pure sulfoxides from a chiral sulfite. J. Org. Chem. 56, 5991–5999 (1991).
Fernandez, I., Khiar, N., Llera, J. M. & Alcudia, F. Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): An improved and general route to both enantiomerically pure sulfoxides. J. Org. Chem. 57, 6789–6796 (1992).
Evans, D. A. et al. Asymmetric synthesis of chiral organosulfur compounds using N-sulfinyloxazolidinones. J. Am. Chem. Soc. 114, 5977–5985 (1992).
Oppolzer, W., Froelich, O., Wiaux-Zamar, C. & Bernardinelli, G. Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam. Tetrahedron Lett. 38, 2825–2828 (1997).
Han, Z., Krishnamurthy, D., Grover, P., Fang, Q. K. & Senanayake, C. H. Properly designed modular asymmetric synthesis for enantiopure sulfinamide auxiliaries from N-sulfonyl-1,2,3-oxathiazolidine-2-oxide agents. J. Am. Chem. Soc. 124, 7880–7881 (2002).
Cogan, D. A., Liu, G., Kim, K., Backes, B. J. & Ellman, J. A. Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines. J. Am. Chem. Soc. 120, 8011–8019 (1998).
Evans, J. W., Fierman, M. B., Miller, S. J. & Ellman, J. A. Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride. J. Am. Chem. Soc. 126, 8134–8135 (2004).
Peltier, H. M., Evans, J. W. & Ellman, J. A. Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts. Org. Lett. 7, 1733–1736 (2005).
Shibata, N. et al. Cinchona alkaloid/sulfinyl chloride combinations: Enantioselective sulfinylating agents of alcohols. J. Am. Chem. Soc. 127, 1374–1375 (2005).
Liao, M. et al. Enantioselective sulfinylation of alcohols and amines by condensation with sulfinates. Chem 10, 1–12 (2024).
Li, B. et al. Catalyst control over S(IV)-stereogenicity via carbene-derived sulfinyl azolium intermediates. J. Am. Chem. Soc. 146, 25350–25360 (2024).
Xiong, Q. et al. Asymmetric synthesis of S(IV)-stereogenic sulfinimidate esters by sulfinamide activation. Angew. Chem. Int. Ed. 64, e202500170 (2025).
Zhang, X., Ang, E. C. X., Yang, Z., Kee, C. W. & Tan, C.-H. Synthesis of chiral sulfinate esters by asymmetric condensation. Nature 604, 298–303 (2022).
Wei, T., Wang, H.-L., Tian, Y., Xie, M.-S. & Guo, H.-M. Enantioselective construction of stereogenic-at-sulfur(IV) centres via catalytic acyl transfer sulfinylation. Nat. Chem. 16, 1301–1311 (2024).
Huang, S. et al. Organocatalytic asymmetric deoxygenation of sulfones to access chiral sulfinyl compounds. Nat. Chem. 15, 185–193 (2023).
Dong, S. et al. Organocatalytic kinetic resolution of sulfoximines. J. Am. Chem. Soc. 138, 2166–2169 (2016).
Wang, J., Frings, M. & Bolm, C. Iron-catalyzed imidative kinetic resolution of racemic sulfoxides. Chem. Eur. J. 20, 966–969 (2014).
Peng, Z. et al. Enantioselective sulfur(VI) fluoride exchange reaction of iminosulfur oxydifluorides. Nat. Chem. 16, 353–362 (2024).
Liu, H. et al. Acid-catalyzed highly enantioselective synthesis of α-amino acid derivatives from sulfinamides and alkynes. Org. Lett. 26, 1601–1606 (2024).
Zou, X. et al. Strain-promoted s-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes. Sci. China Chem. 67, 928–935 (2024).
Zou, X., Wang, H. & Gao, B. Synthesis of sulfoximines by copper-catalyzed oxidative coupling of sulfinamides and aryl boronic acids. Org. Lett. 25, 7656–7660 (2023).
Ma, L.-J. et al. Chiral Brønsted-acid-catalyzed asymmetric oxidation of sulfenamide by using H2O2: A versatile access to sulfinamide and sulfoxide with high enantioselectivity. ACS Catal. 9, 1525–1530 (2019).
Sigman, M. S. & Jacobsen, E. N. Schiff base catalysts for the asymmetric strecker reaction identified and optimized from parallel synthetic libraries. J. Am. Chem. Soc. 120, 4901–4902 (1998).
Malerich, J. P., Hagihara, K. & Rawal, V. H. Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. J. Am. Chem. Soc. 130, 14416–14417 (2008).
Greenhalgh, M. D., Taylor, J. E. & Smith, A. D. Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions. Tetrahedron 74, 5554–5560 (2018).
Okino, T., Hoashi, Y. & Takemoto, Y. Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. J. Am. Chem. Soc. 125, 12672–12673 (2003).
