2,2′-Dihydroxy-1,1′-binaphthalene (BINOL): A chiral C2-symmetric ligand for stereoselective carbon-carbon bond froming reactions

1997; Wiley; Volume: 339; Issue: 1 Linguagem: Inglês

10.1002/prac.199733901138

ISSN

0941-1216

Autores

Reinhold Zimmer, Jutta Suhrbier,

Tópico(s)

Molecular spectroscopy and chirality

Resumo

Journal für Praktische Chemie/Chemiker-ZeitungVolume 339, Issue 1 p. 758-762 The Reagent 2,2′-Dihydroxy-1,1′-binaphthalene (BINOL): A chiral C2-symmetric ligand for stereoselective carbon–carbon bond froming reactions Dr. Reinhold Zimmer, Corresponding Author Dr. Reinhold Zimmer [email protected] Dresden, Institut für Organische Chemie der Technischen UniversitätTechnische Universität Dresden, Institut für Organische Chemie, Mommsenstrasse 13, D-01062 DresdenSearch for more papers by this authorJutta Suhrbier, Jutta Suhrbier Dresden, Institut für Organische Chemie der Technischen UniversitätSearch for more papers by this author Dr. Reinhold Zimmer, Corresponding Author Dr. Reinhold Zimmer [email protected] Dresden, Institut für Organische Chemie der Technischen UniversitätTechnische Universität Dresden, Institut für Organische Chemie, Mommsenstrasse 13, D-01062 DresdenSearch for more papers by this authorJutta Suhrbier, Jutta Suhrbier Dresden, Institut für Organische Chemie der Technischen UniversitätSearch for more papers by this author First published: 25 October 2004 https://doi.org/10.1002/prac.199733901138Citations: 20AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat References 1(a) Reviews: C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; (b) O. Reiser, Nachr. Chem. Techn. Lab. 44 (1996) 380; (c) R. Noyori in Asymmetric Catalysis in Organic Synthesis, Wiley and Sons, New York 1994 2(a) Some selected preparations of (R)- and ( S)-1: F. Toda, K. Tanaka, S. Nagamatsu, Tetrahedron Lett. 25 (1984) 4929; (b) J. Brussee, J. L. G. Groenendijk, J. M. te Koppele, A. C. A. Jansen, Tetrahedron 41 (1985) 3313; (c) L. K. Truedale, Org. Synth. 67 (1989) 13; (d) Y. Tamai, P. Heung-cho, K. Iizuka, A. Okamura, S. Miyano, Synthesis 1990, 222; (e) B.-Q. Gong, W.-Y. Chen, B.-F. Hu, J. Org. Chem. 56 (1991) 423; (f) M. Smràina, J. Poláková, S. Vyskoéil, P. Koéovský, J. Org. Chem. 58 (1993) 4534; (g) M. Kawashima, R. Hirata, Bull. Chem. Soc. Jpn. 66 (1993) 2002; (h) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 58 (1993) 1748; (i) J.-M. Brunel, G. Buono, J. Org. Chem. 58 (1993) 7313; (j) F. Toda, K. Tanaka, Z. Stein, I. Goldberg, J. Org. Chem. 59 (1994) 5748; (k) B. H. Lipshutz, F. Kayser, Z.-P. Li, Angew. Chem. 106 (1994) 1962; (l) M. Nakajima, K. Kanayama, I. Miyoshi, S.-I. Hashimoto, Tetrahedron Lett. 36 (1995) 9519; (m) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 36 (1995) 7991; (n) H.-F. Chow, C.-W. Wan, M.-K. Ng, J. Org. Chem. 61 (1996) 8712; (o) Z. Shan, G. Wang, B. Duan, D. Zhao, Tetrahedron: Asymmetry 7 (1996) 2847; (p) Z. Shan, F. Cheng, S. Huang, D. Zhao, Z. Jing, Tetrahedron: Asymmetry 8 (1997) 1175 3(a) S.-H. Wu, L.-Q. Zhang, C.-S. Chen, G. Girdaukas, C. J. Sih, Tetrahedron Lett. 26 (1985) 4323; (b) S. Miyano, K. Kawahara, Y. Inone, H. Hashimoto, Chem. Lett. 1987, 355; (c) M. Inagaki, J. Hiratake, T. Nishioka, J. Oda Agric, Biol. Chem. 53 (1989) 1879; (d) R. J. Kazlauskas, J. Am. Chem. Soc. 111 (1989) 4953; (e) G. Lin, S.-H. Liu, S.-J. Chen, F.-C. Wu, H.-L. Sun, Tetrahedron Lett. 34 (1993) 6057 4(a) L. Venkatraman, M. Periasamy, Tetrahedron: Asymmetry 7 (1996) 2471; (b) M. Periasamy, L. Venkatraman, K. R. J. Thomas, J. Org. Chem. 62 (1997) 4302 5(a) G. E. Keck, K. H. Tarbet, L. S. Geraci, J. Am. Chem. Soc. 115 (1993) 8467; (b) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 58 (1993) 6543; (c) G. E. Keck, L. S. Geraci, Tetrahedron Lett. 34 (1993) 7827; (d) G. E. Keck, D. Krishnamurthy, J. Am. Chem. Soc. 117 (1995) 2363; and ref. therein 6(a) K. Mikami, S. Narisava, T. Nakai, Synlett 1992, 255; (b) K. Mikami, T. Yajima, M. Terada, T. Uchimara, Tetrahedron Lett. 34 (1993) 7591; (c) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 116 (1994) 4077; (d) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 6 (1995) 2571; (e) K. Mikami, A. Yoshida, Synlett 1995, 29; (f) M. Terada, K. Mikami, J. Chem. Soc., Chem. Commun. 1995, 2391; (g) M. Terada, N. Saya, K. Mikami, Synlett 1995, 411; (h) K. Mikami, T. Yajima, T. Takasaki, S. Matsukawa, M. Terada, T. Uchimara, M. Maruta, Tetrahedron 52 (1996) 85; (i) K. Mikami, T. Yajima, M. Terada, S. Kawauchi, Y. Suzuki, I. Kobayashi, Chem. Lett. 1996, 861; (j) K. Mikami, T. Yajima, N. Siree, M. Terada, Y. Suzuki, I. Kobayashi, Synlett 1996, 837; (k) K. Mikami, S. Matsukawa, E. Sawa, A. Harada, N. Koga, Tetrahedron Lett. 38 (1997) 1951; (l) K. Mikami, S. Matsukawa, M. Nagashima, H. Funabashi, H. Morishima, Tetrahedron Lett. 38 (1997) 579; (m) M. Terada, Y. Matsumoto, Y. Nakamura, K. Mikami, Chem. Commun. 1997, 281; and ref. therein 7 A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 115 (1993) 7001 8 S. Weigand, R. Brükner, Chem. Eur. J. 2 (1996) 1077 9 H. Mayr, M. Patz, Angew. Chem. 106 (1994) 990 10 D. R. Gauthier, Jr., E. M. Carreira, Angew. Chem. 108 (1996) 2521 11 J. W. Faller, D. W. I. Sams, X. Liu, J. Am. Chem. Soc. 118 (1996) 1217 12(a) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 37 (1996) 7095; (b) C.-M. Yu, H.-S. Choi, S.-K. Yoon, W.-H. Jung, Synlett 1997, 889; (c) see also: C.-M. Yu, H.-S. Choi, W.-H. Jung, H.-J. Kim, J. Shin, Chem. Commun. 1997, 761; (d) C.-M. Yu, S.-K. Yoon, H.-S. Choi, K. Baek, Chem. Commun. 1997, 763 13 E. J. Corey, D. Barnes-Seeman, T. W. Lee, Tetrahedron Lett. 38 (1997) 1699 14 K. K. Majumdar, Tetrahedron: Asymmetry 8 (1997) 2079 15 P. Bedeschi, S. Casolari, A. L. Costa, E. Tagliavini, A. Umani-Ronchi, Tetrahedron Lett. 36 (1995) 7897 16 K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 116 (1994) 10520 17 Q. S. Hu, X.-F. Zheng, L. Pu, J. Org. Chem. 61 (1996) 5200 18(a) S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 116 (1994) 4083; (b) S. Kobayashi, M. Araki, I. Hachiya, J. Org. Chem. 59 (1994) 3758 19 For some interesting applications of metal/BINOL catalyst in cycloadditions reported recently, see: (a) R. Lock, H. Waldmann, Chem. Eur. J. 3 (1997) 143; (b) H. Ishitani, S. Kobayashi, Tetrahedron Lett. 37 (1996) 7357; (c) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 118 (1996) 3049; (d) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967; (e) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 116 (1994) 1561 20 I. E. Markó, G. R. Evans, Tetrahedron Lett. 35 (1994) 2771 21 K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 116 (1994) 2812 22 S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 8 (1997) 815 23 G. H. Posner, H. Dai, D. S. Bull, J.-K. Lee, F. Eydoux, Y. Ishihara, W. Welsh, N. Pryor, S. Petr Jr., J. Org. Chem. 61 (1996) 671 24 T. Hanamoto, H. Furuno, Y. Sugimoto, J. Inanaga, Synlett 1997, 79 25 A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2373 26 S. Yamzaki, M. Tanaka, S. Yamabe, J. Org. Chem. 61 (1996) 4046 27 H. Kitajima, K. Ito, Y. Aoki, T. Katsuki, Bull. Chem. Soc. Jpn. 70 (1997) 207 28 M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 109 (1997) 1291 29 K. Ishihara, M. Kaneeda, H. Yamamoto, J. Am. Chem. Soc. 116 (1994) 11179 Citing Literature Volume339, Issue11997Pages 758-762 ReferencesRelatedInformation

Referência(s)
Altmetric
PlumX