Design and preparation of 3,3'-disubstituted 2,2'-bis(oxazolyl)-1,1'- binaphthyls (boxax): New chiral bis(oxazoline) ligands for catalytic asymmetric Wacker-type cyclization

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1620-1625

  Uozumi, Yasuhiro ^a   Kyota, Hirokazu ^b   Kato, Kazuhiko ^b   Ogasawara, Masamichi ^b   Hayashi, Tamio ^b  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 METHYL 2 BUTENYL)PHENOL; 2 ETHENYL 2 METHYL 2,3 DIHYDROBENZOFURAN; 2,2' BIS(4,4 DIMETHYLOXAZOL 2 YL) 3,3' BIS(METHOXYCARBONYL) 1,1' BINAPHTHYL; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; CYCLIZATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033525716     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982104m     Document Type: Article

References (21)

1. For recent reviews on catalytic asymmetric reactions, see: (a) Brunner, H. Synthesis 1988, 645.
2. (b) Brunner, H. Top. Stereochem. 1988, 18, 129.
3. (c) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
4. (d) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: New York, 1989; Vol. 5, p 115.
5. (e) Ojima, I.; Clos, N.; Bastos, C. Tetrahedron 1989, 45, 6901.
6. (f) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH, Inc.: New York, 1993.
7. (g) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
8. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds.: VCH: Weinheim, 1995; p 105.
9. (b) Hayashi, T. J. Synth. Org. Chem., Jpn. 1994, 52, 900.
10. (c) Hayashi, T. Acta Chem. Scand. 1996, 50, 259.
11. (a) Uozumi, Y.; Kyota, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron Asymmetry 1996, 7, 1603.
12. (b) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.
13. (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Org. Chem. 1998, 63, 5071.
14. For reviews on ortho-lithiation, see: (a) Wakefield, B. J Organolithium Methods; Academic Press: London, 1988.
15. (b) Millan, J. M.; Bebb, R. L. Chem. Rev. 1969, 69, 693.
16. (c) Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1.
17. For example of ortho-lithiation of aromatic compounds directed by oxazolyl group, see: (d) Carpenter, A. J.; Chadwick, D. J. J. Chem. Soc., Perkin Trans. 1 1985, 173.
18. Ohta, T.; Ito, M.; Inagaki, K.; Takaya, H. Tetrahedron Lett. 1993, 34, 1615.
19. Hosokawa, T.; Imada, Y.; Murahashi, S.-I. Bull. Chem. Soc. Jpn. 1985, 58, 3282.
20. For recent examples of asymmetric oxidations catalyzed by palladium(II): (a) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790.
21. (b) Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.