A new method for optical resolution of BINOL by molecular complexation with (S)-5-oxopyrrolidine-2-carboxanilide

Author:

Du Haifeng,Ji Baoming,Wang Yang,Sun Jie,Meng Jiben,Ding Kuiling

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference10 articles.

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3. For the application to the synthesis of materials, see: Ref. 1e. For other examples, see: (a) Aragi, K.; Piao, G.; Kaneko, S.; Sakamaki, K.; Shirakawa, H.; Kyotani, M. Science 1998, 282, 1683–1686; (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 120–121; (c) Zhang, M.; Schuster, G. B. J. Am. Chem. Soc. 1994, 116, 4852–4857; (d) Deussen, H.-J.; Hendrickx, E.; Boutton, C.; Krog, D.; Clays, K.; Bechgaard, K.; Persoons, A.; Bjornholm, T. J. Am. Chem. Soc. 1996, 118, 6841–6852; (e) Musick, K. Y.; Hu, Q. S.; Pu, L. Macromolecules 1998, 31, 2933–2942; (f) Wong, M. S.; Nicoud, J.-F. J. Chem. Soc., Chem. Commun. 1994, 249–250; (g) Meng, Y.; Slaven, W. T.; Wang, D.; Liu, T. J.; Chow, H. F.; Li, C. J. Tetrahedron: Asymmetry 1998, 9, 3693–3707.

4. For the resolution of 1 through formation of diastereoisomers, see: (a) Jacques, J.; Fouquey, C.; Viterbo, R. Tetrahedron Lett. 1971, 7, 4617–4620; (b) Jacques, J.; Fouquey, C. Org. Synth. 1988, 67, 1–12; (c) Gong, B.; Chen, W.; Hu, B. J. Org. Chem. 1991, 56, 423–425; (d) Brunel, J. M.; Buono, G. J. Org. Chem. 1993, 58, 7313–7314; (e) Wang, M.; Liu, S.; Hu, B. J. Org. Chem. 1995, 60, 7364–7265; (f) Fabbri, D.; Deloga, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599–6601; (g) Pakulski, Z.; Zamojski, A. Tetrahedron: Asymmetry 1995, 6, 111–115; (h) Chow, H. F.; Wan, C. W.; Ng, M. K. J. Org. Chem. 1996, 61, 8712–8714; (i) Kim, H. C.; Choi, S.; Kim, H.; Ahn, K. H.; Koh, J. H.; Park, J. Tetrahedron Lett. 1997, 38, 3959–3962; (j) Shan, Z.; Xiong, Y.; Zhao, D. Tetrahedron 1999, 55, 3893–3896; (k) Shan, Z.; Wang, G.; Duan, B.; Zhao, D. Tetrahedron: Asymmetry 1996, 7, 2847–2850; (l) Shan, Z.; Cheng, F.; Huang, S.; Zhao, D.; Jing, Z. Tetrahedron: Asymmetry 1997, 8, 1175–1177; (j) Periasamy, M.; Venkatraman, L.; Sivakumar, S.; Sampathkumar, N.; Ramanathan, C. R. J. Org. Chem. 1999, 64, 7643–7645.

5. For the resolution of 1 through molecular complexation, see: (a) Tanaka, K.; Okada, T.; Toda, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1147–1148; (b) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748–5751; (c) Toda, F.; Tanaka, K. Chem. Commun. 1997, 1087–1088; (d) Cai, D. W.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991–7994; (e) Hu, Q. S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123–2126; (f) Wang, Y.; Sun, J.; Ding, K. Tetrahedron 2000, 56, 4447–4451; (g) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299–2300; (h) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002–2005; (i) Periasamy, M.; Prasad, A. S. B.; Kanth, J. V. B.; Reddy, Ch. K. Tetrahedron: Asymmetry 1995, 6, 341–344; (j) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302–4306.

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