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Spiro indane-based phosphine–oxazoline ligands for palladium-catalyzed asymmetric arylation of cyclic N-sulfonyl imines

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Abstract

Palladium complexes of indane-based phosphine–oxazoline ligands with a spirocarbon stereogenic center were examined for asymmetric addition of arylboronic acids to cyclic N-sulfonyl imines. Excellent reaction activities (up to 99% yield) and enantioselectivities (up to 99% ee) were obtained with a broad scope of substrate.

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References

  1. Wagstaff AJ, Ormrod D, Spencer CM (2001) CNS Drugs 15:231–259

    Article  CAS  Google Scholar 

  2. Pflum DA, Krishnamurthy D, Han Z, Wald SA, Senanayake DH (2002) Tetrahedron Lett 43:923–926

    Article  CAS  Google Scholar 

  3. Stocchi F, Fossati C, Torti M (2015) Expert Opin Pharmacother 16:2231–2241

    Article  Google Scholar 

  4. Wang H, Xu MH (2013) Synthesis 45:2125–2133

    Article  CAS  Google Scholar 

  5. Wang H, Jiang T, Xu MH (2013) J Am Chem Soc 135:971–974

    Article  CAS  Google Scholar 

  6. Jiang T, Wang Z, Xu MH (2015) Org Lett 17:528–531

    Article  CAS  Google Scholar 

  7. Xie L, Ma HL, Li JQ, Yu Y, Qin ZH, Fu B (2017) Org Chem Front 4:1858–1862

    Article  CAS  Google Scholar 

  8. Quan M, Tang L, Shen JQ, Yang GQ, Zhang WB (2017) Chem Commun 53:609–612

    Article  CAS  Google Scholar 

  9. Sun WY, Gu HR, Lin XF (2018) J Org Chem 83:4034–4043

    Article  CAS  Google Scholar 

  10. Yang GQ, Zhang WB (2013) Angew Chem 125:7688–7692

    Article  Google Scholar 

  11. Quan M, Yang GQ, Xie F, Gridnev ID, Zhang WB (2015) Org Chem Front 2:398–402

    Article  CAS  Google Scholar 

  12. Álvarez-Casao Y, Monge D, Álvarez E, Fernández R, Lassaletta JM (2015) Org Lett 17:5104–5107

    Article  Google Scholar 

  13. Zhang ZF, Butt NA, Zhang WB (2016) Chem Rev 116:14769–14827

    Article  CAS  Google Scholar 

  14. Pellissier H (2016) Chem Rev 116:14868–14917

    Article  CAS  Google Scholar 

  15. Jiang CH, Lu YX, Hayashi T (2014) Angew Chem Int Ed 53:9936–9939

    Article  CAS  Google Scholar 

  16. Zhou B, Li KZ, Jiang CH, Lu YX, Hayashi T (2017) Adv Synth Catal 359:1969–1975

    Article  CAS  Google Scholar 

  17. Zhu SF, Xie JB, Zhang YZ, Li S, Zhou QL (2006) J Am Chem Soc 128:12886–12891

    Article  CAS  Google Scholar 

  18. Li S, Zhu SF, Zhang CM, Song S, Zhou QL (2008) J Am Chem Soc 130:8584–8585

    Article  CAS  Google Scholar 

  19. Li S, Zhu SF, Xie JH, Song S, Zhang CM, Zhou QL (2010) J Am Chem Soc 132:1172–1179

    Article  CAS  Google Scholar 

  20. Song S, Zhu SF, Yang S, Li S, Zhou QL (2012) Angew Chem Int Ed 51:2708–2711

    Article  CAS  Google Scholar 

  21. Song S, Zhu SF, Pu LY, Zhou QL (2013) Angew Chem Int Ed 52:6072–6075

    Article  CAS  Google Scholar 

  22. Song S, Zhu SF, Yu YB, Zhou QL (2013) Angew Chem Int Ed 52:1556–1559

    Article  CAS  Google Scholar 

  23. Han ZB, Wang Z, Wang XM, Ding KL (2009) Angew Chem Int Ed 48:5345–5349

    Article  CAS  Google Scholar 

  24. Zhang Y, Han ZB, Li FY, Ding KL, Zhang A (2010) Chem Commun 46:156–158

    Article  CAS  Google Scholar 

  25. Shang J, Han ZB, Li Y, Wang Z, Ding KL (2012) Chem Commun 48:5172–5174

    Article  CAS  Google Scholar 

  26. Wang XM, Han ZB, Wang Z, Ding KL (2012) Angew Chem Int Ed 51:936–940

    Article  CAS  Google Scholar 

  27. Qiu ZX, Sun R, Teng DW (2018) Org Biomol Chem 16:7717–7724

    Article  CAS  Google Scholar 

  28. Gao YF, Qiu ZX, Sun R, Gao NX, Cao GR, Teng DW (2018) Tetrahedron Lett 59:3938–3941

    Article  CAS  Google Scholar 

  29. Duan Y, Li L, Chen MW, Yu CB, Fan HJ, Zhou YG (2014) J Am Chem Soc 136:7688–7700

    Article  CAS  Google Scholar 

  30. Hepburn HB, Lam HW (2014) Angew Chem Int Ed 53:11605–11610

    Article  CAS  Google Scholar 

  31. Davis FA, Towson JC, Vashi DB, ThimmaReddy R, McCauley JP Jr, Harakal ME, Gosciniak DJ (1990) J Org Chem 55:1254–1261

    Article  CAS  Google Scholar 

  32. Nishimura T, Noishiki A, Tsui GC, Hayashi T (2012) J Am Chem Soc 134:5056–5059

    Article  CAS  Google Scholar 

  33. Wang YQ, Yu CB, Wang DW, Wang XB, Zhou YG (2008) Org Lett 10:2071–2074

    Article  CAS  Google Scholar 

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Correspondence to Dawei Teng.

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Qiu, Z., Li, Y., Zhang, Z. et al. Spiro indane-based phosphine–oxazoline ligands for palladium-catalyzed asymmetric arylation of cyclic N-sulfonyl imines. Transit Met Chem 44, 649–654 (2019). https://doi.org/10.1007/s11243-019-00329-z

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  • DOI: https://doi.org/10.1007/s11243-019-00329-z

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