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.
Similar content being viewed by others
References
Wagstaff AJ, Ormrod D, Spencer CM (2001) CNS Drugs 15:231–259
Pflum DA, Krishnamurthy D, Han Z, Wald SA, Senanayake DH (2002) Tetrahedron Lett 43:923–926
Stocchi F, Fossati C, Torti M (2015) Expert Opin Pharmacother 16:2231–2241
Wang H, Xu MH (2013) Synthesis 45:2125–2133
Wang H, Jiang T, Xu MH (2013) J Am Chem Soc 135:971–974
Jiang T, Wang Z, Xu MH (2015) Org Lett 17:528–531
Xie L, Ma HL, Li JQ, Yu Y, Qin ZH, Fu B (2017) Org Chem Front 4:1858–1862
Quan M, Tang L, Shen JQ, Yang GQ, Zhang WB (2017) Chem Commun 53:609–612
Sun WY, Gu HR, Lin XF (2018) J Org Chem 83:4034–4043
Yang GQ, Zhang WB (2013) Angew Chem 125:7688–7692
Quan M, Yang GQ, Xie F, Gridnev ID, Zhang WB (2015) Org Chem Front 2:398–402
Álvarez-Casao Y, Monge D, Álvarez E, Fernández R, Lassaletta JM (2015) Org Lett 17:5104–5107
Zhang ZF, Butt NA, Zhang WB (2016) Chem Rev 116:14769–14827
Pellissier H (2016) Chem Rev 116:14868–14917
Jiang CH, Lu YX, Hayashi T (2014) Angew Chem Int Ed 53:9936–9939
Zhou B, Li KZ, Jiang CH, Lu YX, Hayashi T (2017) Adv Synth Catal 359:1969–1975
Zhu SF, Xie JB, Zhang YZ, Li S, Zhou QL (2006) J Am Chem Soc 128:12886–12891
Li S, Zhu SF, Zhang CM, Song S, Zhou QL (2008) J Am Chem Soc 130:8584–8585
Li S, Zhu SF, Xie JH, Song S, Zhang CM, Zhou QL (2010) J Am Chem Soc 132:1172–1179
Song S, Zhu SF, Yang S, Li S, Zhou QL (2012) Angew Chem Int Ed 51:2708–2711
Song S, Zhu SF, Pu LY, Zhou QL (2013) Angew Chem Int Ed 52:6072–6075
Song S, Zhu SF, Yu YB, Zhou QL (2013) Angew Chem Int Ed 52:1556–1559
Han ZB, Wang Z, Wang XM, Ding KL (2009) Angew Chem Int Ed 48:5345–5349
Zhang Y, Han ZB, Li FY, Ding KL, Zhang A (2010) Chem Commun 46:156–158
Shang J, Han ZB, Li Y, Wang Z, Ding KL (2012) Chem Commun 48:5172–5174
Wang XM, Han ZB, Wang Z, Ding KL (2012) Angew Chem Int Ed 51:936–940
Qiu ZX, Sun R, Teng DW (2018) Org Biomol Chem 16:7717–7724
Gao YF, Qiu ZX, Sun R, Gao NX, Cao GR, Teng DW (2018) Tetrahedron Lett 59:3938–3941
Duan Y, Li L, Chen MW, Yu CB, Fan HJ, Zhou YG (2014) J Am Chem Soc 136:7688–7700
Hepburn HB, Lam HW (2014) Angew Chem Int Ed 53:11605–11610
Davis FA, Towson JC, Vashi DB, ThimmaReddy R, McCauley JP Jr, Harakal ME, Gosciniak DJ (1990) J Org Chem 55:1254–1261
Nishimura T, Noishiki A, Tsui GC, Hayashi T (2012) J Am Chem Soc 134:5056–5059
Wang YQ, Yu CB, Wang DW, Wang XB, Zhou YG (2008) Org Lett 10:2071–2074
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
There are no conflicts to declare.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-019-00329-z