Abstract
A set of chiral sulfinyl imine–thioether ligands are prepared via dehydration condensation of substituted benzaldehyde and chiral sulfinamide. The activity of these ligands in Pd-catalyzed asymmetric allylic alkylation reaction is studied, and the results indicate that the structure of sulfinamide motifs has an obvious effect on the e.r. value and yield. The chiral p-tolylsulfinamide derived ligands can promote the reaction efficiently, while the ligands with tert-butyl group fail to catalyze the reaction. Then, the substrate scope is also investigated under the optimal reaction conditions.
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References
Arrayás RG, Carretero JC (2011) Chiral thioether-based catalysts in asymmetric synthesis: recent advances. Chem Commun 47:2207–2211. https://doi.org/10.1039/c0cc03978k
Chen P, Su X, Zhou W, Xiao Y, Zhang J (2016) Novel chiral sulfinamide phosphines: valuable precursors to chiral β-aminophosphines. Tetrahedron 72:2700–2706. https://doi.org/10.1016/j.tet.2015.12.002
Christman M, Bräse S (2008) Asymmetric synthesis-the essentials, 2nd edn. Wiley, Weinheim
Dong HQ, Xu MH, Feng CG, Sun XW, Lin GQ (2015) Recent applications of chiral N-tert-butanesulfinyl imines, chiral diene ligands and chiral sulfur–olefin ligands in asymmetric synthesis. Org Chem Front 2:73–89. https://doi.org/10.1039/c4qo00245h
Ellman JA, Owens TD, Tang TP (2002) N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines. Acc Chem Res 35:984–995. https://doi.org/10.1021/ar020066u
Feng X, Wang Y, Wei B, Yang J, Du H (2011a) Simple N-sulfinyl-based chiral sulfur-olefin ligands for rhodium-catalyzed asymmetric 1,4-additions. Org Lett 13:3300–3303. https://doi.org/10.1021/ol2009494
Feng X, Wei B, Yang J, Du H (2011b) Chiral N-tert-butanesulfinyl alpha, beta-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions. Org Biomol Chem 9:5927–5929. https://doi.org/10.1039/c1ob05971h
Feng X, Nie Y, Yang J, Du H (2012) Rh(I)-catalyzed asymmetric 1,2-addition to alpha-diketones with chiral sulfur-alkene hybrid ligands. Org Lett 14:624–627. https://doi.org/10.1021/ol203238j
Ferreira F, Botuha C, Chemla F, Pérez-Luna A (2009) tert-Butanesulfinimines: structure, synthesis and synthetic applications. Chem Soc Rev 38:1162–1186. https://doi.org/10.1039/b809772k
Gan Z, Zhi M, Han R, Li EQ, Duan Z, Mathey F (2019) P-stereogenic phosphines directed copper(I)-catalyzed enantioselective 1,3-dipolar cycloadditions. Org Lett 21:2782–2785. https://doi.org/10.1021/acs.orglett.9b00734
Jacobsen EN, Pfaltz A, Yamamoto H (1999) Comprehensive asymmetric catalysis. Springer, Berlin
Jin SS, Wang H, Xu MH (2011) Design of N-sulfinyl homoallylic amines as novel sulfinamide-olefin hybrid ligands for asymmetric catalysis: application in Rh-catalyzed enantioselective 1,4-additions. Chem Commun 47:7230–7232. https://doi.org/10.1039/c1cc12322j
Jin SS, Wang H, Zhu TS, Xu MH (2012) Design of N-cinnamyl sulfinamides as new sulfur-containing olefin ligands for asymmetric catalysis: achieving structural simplicity with a categorical linear framework. Org Biomol Chem 10:1764–1768. https://doi.org/10.1039/c2ob06723d
Li Y, Xu MH (2014) Simple sulfur-olefins as new promising chiral ligands for asymmetric catalysis. Chem Commun 50:3771–3782. https://doi.org/10.1039/c3cc49431d
Li W, Zhang J (2016) Recent developments in the synthesis and utilization of chiral beta-aminophosphine derivatives as catalysts or ligands. Chem Soc Rev 45:1657–1677. https://doi.org/10.1039/c5cs00469a
Liu Y, Li W, Zhang J (2017) Chiral ligands designed in China. Natl Sci Rev 4:326–358. https://doi.org/10.1093/nsr/nwx064
Masdeu-Bultó AM, Diéguez M, Martin E, Gómez M (2003) Chiral thioether ligands: coordination chemistry and asymmetric catalysis. Coord Chem Rev 242:159–201. https://doi.org/10.1016/s0010-8545(03)00106-1
Mellah M, Voituriez A, Schulz E (2007) Chiral sulfur ligands for asymmetric catalysis. Chem Rev 107:5133–5209. https://doi.org/10.1021/cr068440h
Mendes JA, Costa PRR, Yus M, Foubelo F, Buarque CD (2021) N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles. Beilstein J Org Chem 17:1096–1140. https://doi.org/10.3762/bjoc.17.86
Mikami K, Lautens M (2007) New frontiers in asymmetric catalysis. Wiley, New York
Morton D, Stockman RA (2006) Chiral non-racemic sulfinimines: versatile reagents for asymmetric synthesis. Tetrahedron 62:8869–8905. https://doi.org/10.1016/j.tet.2006.06.107
Noyori R (1994) Asymmetric Catalysis in Organic Synthesis. Wiley, New York
Ojima I (2010) Catalytic asymmetric synthesis, 3rd edn. Wiley, New York
Omann L, Königs CDF, Klare HFT, Oestreich M (2017) Cooperative catalysis at metal-sulfur bonds. Acc Chem Res 50:1258–1269. https://doi.org/10.1021/acs.accounts.7b00089
Otocka S, Kwiatkowska M, Madalińska L, Kielbasiński P (2017) Chiral organosulfur ligands/catalysts with a stereogenic sulfur atom: applications in asymmetric synthesis. Chem Rev 117:4147–4181. https://doi.org/10.1021/acs.chemrev.6b00517
Owens TD, Hollander FJ, Oliver AG, Ellman JA (2001) Synthesis, utility, and structure of novel bis(sulfinyl)imidoamidine ligands for asymmetric lewis acid catalysis. J Am Chem Soc 123:1539–1540. https://doi.org/10.1021/ja005635c
Pellissier H (2007) Chiral sulfur-containing ligands for asymmetric catalysis. Tetrahedron 63:1297–1330. https://doi.org/10.1016/j.tet.2006.09.068
Philip RM, Treesa GSS, Saranya S, Anilkumar G (2021) Applications of aryl-sulfinamides in the synthesis of N-heterocycles. RSC Adv 11:20591–20600. https://doi.org/10.1039/d1ra04099e
Qi WY, Zhu TS, Xu MH (2011) Design of chiral sulfoxide-olefins as a new class of sulfur-based olefin ligands for asymmetric catalysis. Org Lett 13:3410–3413. https://doi.org/10.1021/ol201151r
Revu O, Uphade MB, Prasad KR (2016) Synthesis and evaluation of C2-symmetric bis-sulfinamides as effective ligands in rhodium catalyzed addition of arylboronic acids to cycloalkenones. Tetrahedron 72:5355–5362. https://doi.org/10.1016/j.tet.2016.07.024
Robak MT, Herbage MA, Ellman JA (2010) Synthesis and applications of tert-butanesulfinamide. Chem Rev 110:3600–3740. https://doi.org/10.1021/cr900382t
Schenkel LB, Ellman JA (2003) Novel sulfinyl imine ligands for asymmetric catalysis. Org Lett 5:545–548. https://doi.org/10.1021/ol027468m
Uphade MB, Reddy AA, Khandare SP, Prasad KR (2019) Stereoselective addition of a lithium anion of 1,1-diphenyl-2-aza-pentadiene to sulfinimines: application to the synthesis of (-)-epiquinamide. Org Lett 21:9109–9113. https://doi.org/10.1021/acs.orglett.9b03507
Wang H, Zhu TS, Xu MH (2012) Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl alpha-ketoesters for synthesis of heteroaromatic alpha-hydroxy esters. Org Biomol Chem 10:9158–9164. https://doi.org/10.1039/c2ob26316e
Wang H, Jiang T, Xu MH (2013) Simple branched sulfur-olefins as chiral ligands for Rh-catalyzed asymmetric arylation of cyclic ketimines: highly enantioselective construction of tetrasubstituted carbon stereocenters. J Am Chem Soc 135:971–974. https://doi.org/10.1021/ja3110818
Yoon TP, Jacobsen EN (2003) Privileged chiral catalysts. Science 299:1691–1693. https://doi.org/10.1126/science.1083622
Zhang ZM, Chen P, Li W, Niu Y, Zhao XL, Zhang J (2014) A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantioselective gold(I)-catalyzed cycloaddition reactions. Angew Chem Int Ed 53:4350–4354. https://doi.org/10.1002/anie.201401067
Zhou QL (2011) Privileged chiral ligands and catalysts. Wiley-VCH, Weinheim
Zhou P, Chen BC, Davis FA (2004) Recent advances in asymmetric reactions using sulfinimines (N-sulfinyl imines). Tetrahedron 60:8003–8030. https://doi.org/10.1016/j.tet.2004.06.071
Zhu TS, Jin SS, Xu MH (2012) Rhodium-catalyzed, highly enantioselective 1,2-addition of aryl boronic acids to alpha-ketoesters and alpha-diketones using simple, chiral sulfur-olefin ligands. Angew Chem Int Ed 51:780–783. https://doi.org/10.1002/anie.201106972
Acknowledgements
We are grateful for the financial support from the National Science Foundation of China (No. 21901009), Natural Science Foundation of Guangxi (No. 2019GXNSFBA245075) and the Middle-Aged and Young Teachers' Basic Ability Promotion Project of Guangxi (No. 2019KY0734).
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You, GY., Liu, XF., Fang, PW. et al. Simple chiral sulfinyl imine–thioether ligands for Pd-catalyzed allylic alkylation. Chem. Pap. 76, 4615–4620 (2022). https://doi.org/10.1007/s11696-022-02176-2
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DOI: https://doi.org/10.1007/s11696-022-02176-2