A simple synthetic approach to homochiral 6- and 6′-substituted 1,1′-binaphthyl derivatives

Tetrahedron

Volumn 59, Issue 5, 2003, Pages 619-630

  Hocke, Heiko ^a   Uozumi, Yasuhiro ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

1,1 binaphthyls; Immobilization; Polymer supports

Indexed keywords

HYDROXYL GROUP; MACROGOL DERIVATIVE; NAPHTHOL DERIVATIVE; NAPHTHYL GROUP; POLYMER;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; CYCLIZATION; PRIORITY JOURNAL;

EID: 0037467687     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01584-3     Document Type: Article

References (41)

1. For reviews, see: (a) Rosini C., Franzini L., Raffaelli A., Salvadori P. Synthesis. 1992;503 (b) Ojima I. Catalytic Asymmetric Synthesis. 2000;Wiley-VCH, Weinheim. and references therein.
2. For reviews, see: (a) Rosini C., Franzini L., Raffaelli A., Salvadori P. Synthesis. 1992;503 (b) Ojima I. Catalytic Asymmetric Synthesis. 2000;Wiley-VCH, Weinheim. and references therein.
3. For reviews, see: (a) De Vos D.E., Vankelecom I.F.J., Jacobs P.A. Chiral Catalyst Immobilization and Recycling. 2000;Wiley-VCH, Weinheim. and references cited therein (b) Doerwald F.Z. Organic Synthesis on Solid Phase. 2000;Wiley-VCH, Weinheim.
4. For reviews, see: (a) De Vos D.E., Vankelecom I.F.J., Jacobs P.A. Chiral Catalyst Immobilization and Recycling. 2000;Wiley-VCH, Weinheim. and references cited therein (b) Doerwald F.Z. Organic Synthesis on Solid Phase. 2000;Wiley-VCH, Weinheim.
5. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
6. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
7. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
8. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
9. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
10. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
11. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
12. For recent examples of the immobilization of binaphthyl-based chiral catalysts, see: (a) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. J. Am. Chem. Soc. 120:1998;4051 (b) Nozaki K., Itoi Y., Shibahara F., Shirakawa E., Ohta T., Takaya H., Hiyama T. Bull. Chem. Soc. Jpn. 72:1999;1911 (c) Bayston D.J., Fraser J.L., Ashton M.R., Baxter A.D., Polywka M.E.C., Moses E. J. Org. Chem. 63:1998;3137 (d) Kobayashi S., Kusakabe K., Ishitani H. Org. Lett. 2:2000;1225 (e) Fujii A., Sodeoka M. Tetrahedron Lett. 40:1999;8011 (f) Matsunaga S., Ohshima T., Shibasaki M. Tetrahedron Lett. 41:2000;8473 (g) Nogami H., Matsunaga S., Kanai M., Shibasaki M. Tetrahedron Lett. 42:2001;279 (h) Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801.
13. (a) Kawashima, M.; Kakayama, M. Japan Patent J P 200044504 assigned to Kankyo Kagaku Center K.K., Japan, 2000.
14. (b) De Vanis J.-B.R. Tetrahedron Lett. 42:2001;6507.
15. Asymmetric Wacker-type cyclization with the various immobilized boxax ligands has been reported, see: Hocke H., Uozumi Y. Synlett. 2002;2049.
16. During preparation of this manuscript, controlled monobromination of 1,1′-bi-2-naphthol via the monopivalate 2 was reported, see: Cai D., Larsen R.D., Reider P.J. Tetrahedron Lett. 43:2002;4055.
17. Glaser R., Twaik M. Tetrahedron Lett. 15:1976;1219.
18. Arnold L.A., Imbos R., Mandoli A., de Vries A.H.M., Naasz R., Feringa B.L. Tetrahedron. 56:2000;2865.
19. Brisdon J.B., England R., Reza K., Sainsbury M. Tetrahedron. 49:1993;1103.
20. Uozumi Y., Kyota H., Kishi E., Kitayama K., Hayashi T. Tetrahedron: Asymmetry. 7:1996;1603.
21. (a) Uozumi Y., Kato K., Hayashi T. J. Am. Chem. Soc. 119:1997;5063
22. (b) Uozumi Y., Kato K., Hayashi T. J. Org. Chem. 63:1998;5071
23. (c) Uozumi Y., Kyota H., Hayashi T. J. Org. Chem. 64:1999;1621.
24. (a) Hotta H., Suzuki T., Miyano S., Inoue Y. J. Mol. Cat. 54:1989;L5
25. (b) Ohta T., Ito M., Inagaki K., Takaya H. Tetrahedron Lett. 34:1993;1615.
26. ArgoGel amino resin (1% DVB cross-linked) purchased from Argonaut Technologies Inc. was used.
27. Aminomethylated polystyrene (1% DVB cross-linked) was purchased from Novabiochem.
28. For a copolymerisate of acrylamidopropyl[2-aminopropyl]polyethylene glycol and N,N-dimethylacrylamide crosslinked with bis(2-acrylamidopropyl)poly(ethylene glycol) (PEGA), see: Meldal M. Tetrahedron Lett. 33:1992;3077.
29. MeO-PEG5000 amino resin was purchased from Fluka.
30. For reviews of PEG-supported reagents, see: (a) Sieber F., Wentworth P., Janda K.D. J. Comb. Chem. 1:1999;540 (b) Wentworth P., Janda K.D. Chem. Commun. 1999;1917 (c) Toy P.H., Janda K.D. Acc. Chem. Res. 33:2000;546.
31. For reviews of PEG-supported reagents, see: (a) Sieber F., Wentworth P., Janda K.D. J. Comb. Chem. 1:1999;540 (b) Wentworth P., Janda K.D. Chem. Commun. 1999;1917 (c) Toy P.H., Janda K.D. Acc. Chem. Res. 33:2000;546.
32. For reviews of PEG-supported reagents, see: (a) Sieber F., Wentworth P., Janda K.D. J. Comb. Chem. 1:1999;540 (b) Wentworth P., Janda K.D. Chem. Commun. 1999;1917 (c) Toy P.H., Janda K.D. Acc. Chem. Res. 33:2000;546.
33. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
34. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
35. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
36. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
37. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
38. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
39. 1-symmetric binaphthyl-based chiral catalysts, see: (a) Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887 (b) Uozumi Y., Lee S.-Y., Hayashi T. Tetrahedron Lett. 33:1992;7185 (c) Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y. J. Am. Chem. Soc. 116:1994;775 (d) Uozumi Y., Hayashi T. Tetrahedron Lett. 34:1993;2335 (e) Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 115:1993;7033 (f) Horiuchi T., Ohta T., Nozaki K., Takaya H. Chem. Commun. 1996;155 (g) Sakai N., Nozaki K., Takaya H. J. Chem. Soc., Chem. Commun. 1994;395.
40. Tamai Y., Qian P., Matsunaga K., Miyano S. Bull. Chem. Soc. Jpn. 65:1992;817.
41. Kaiser E., Colescott R.L., Bossinger C.D., Cook P.I. Anal. Biochem. 34:1970;595.