Abstract
A series of chiral bis(oxazoline)thiophenes were used as chiral ligands in the Cu(II)-catalyzed asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes, and the effects of reaction conditions on the yield and enantioselectivity were investigated. The ligand 1c was identified as the best ligand of this family in the same reaction.
Graphical Abstract
Similar content being viewed by others
References
Sundberg RJ (1970) In: The chemistry of indoles. Academic Press, New York
Brown RK (1972) In: Houlihan WJ (ed) Indoles. Wiley-Interscience, New York
Herrea RP, Sgarzani V, Bernardi VL, Ricci A (2005) Angew Chem Int Ed 44:6576
Gaunt MJ, Johansson CCC, McNally A, Vo NT (2007) Drug Discovery Today 12:8
Poulsen TB, Jørgensen KA (2008) Chem Rev 108:2903
Ganesh M, Seidel D (2008) J Am Chem Soc 130:16464
Scettri A, Villano R, Acocella MR (2009) Molecules 14:3030
Terada M (2010) Synthesis 12:1929
Sakamoto T, Itoh J, Mori K, Akiyama T (2010) Org Biomol Chem 8:5448
Rueping M, Nachtsheim BJ (2010) Beilstein J Org Chem 6:1
Kim HY, Kim S, Oh K (2010) Angew Chem Int Ed 49:1
Liu H, Du DM (2010) Adv Synth Catal 352:1113
Guo FF, Lia GY, Xiong SS, Wang SJ, Wang ZY (2010) Chem Eur J 16:6433
Arai T, Awata A, Wasai M, Yokoyama N, Masu H (2011) J Org Chem 76:5450
Lin S, Jacobsen EN (2012) Nat Chem 4:817
Chauhan P, Chimni SS (2012) R Soc Chem Adv 2:6117
Chen LY, Guillarme S, Saluzzo C (2013) Arkivoc 3:227
You SL, Cai Q, Zeng M (2009) Chem Soc Rev 38:2190
Lin SZ, You TP (2009) Tetrahedron 65:1010
Wu LY, Hao XQ, Xu YX, Jia MQ, Wang TN, Gong JF, Song MP (2009) Organometallics 28:3369
McKeon SC, Müller-Bunz H, Guiry PJ (2009) Eur J Org Chem 2009:4833
Yokoyama N, Arai T (2009) Chem Commun 22:3285
Kim HY, Kim S, Oh K (2010) Angew Chem Int Ed 49:4476
Terrasson V, De Figueiredo RM, Campagne JM (2010) Eur J Org Chem 2010:2635
Zeng M, You SL (2010) Synlett 9:1289
Wu J, Li X, Wu F, Wan B (2011) Org Lett 13:4834
McKeon SC, Müller-Bunz H, Guiry PJ (2011) Eur J Org Chem 2011:7107
Hao XQ, Xu YX, Yang MJ, Wang L, Niu JL, Gong JF, Song MP (2012) Organometallics 31:835
Chen LA, Tang X, Xi J, Xu W, Gong L, Meggers E (2013) Angew Chem Int Ed 52:14021
Liu H, Lu SF, Xu J, Du DM (2008) Chem Asian J 3:1111
Liu H, Du DM (2010) Eur J Org Chem 2010:2121
Peng J, Du DM (2012) Eur J Org Chem 2012:4042
Gao JR, Wu H, Xiang B, Yu WB, Han L, Jia YX (2013) J Am Chem Soc 135:2983
Jia YX, Zhu SF, Yang Y, Zhou QL (2006) J Org Chem 71:75
Lu SF, Du DM, Xu J (2006) Org Lett 8:2115
Hargaden GC, Guiry PJ (2009) Chem Rev 109:2505
Desimoni G, Faita G, Jørgensen A (2011) Chem Rev 111:PR284
Gao MZ, Kong DY, Clearfied A, Zingaro RA (2004) Tetrahedron Lett 45:5649
Li WJ, Qiu SX (2010) J Heterocycl Chem 47:1340
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Li, W. Chiral Bis(Oxazolinyl)thiophenes for Enantioselective Cu(II)-Catalyzed Friedel–Crafts Alkylation of Indole Derivatives with Nitroalkenes. Catal Lett 144, 943–948 (2014). https://doi.org/10.1007/s10562-014-1228-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-014-1228-2