Cyclic chiral diols with C2 symmetry: Synthesis of (2R, 3R)-dihydroxy-1,2,3,4-tetrahydronaphthalene

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1033-1040

  Orsini, Fulvia ^a   Pelizzoni, Francesca ^a  

^a Dipto di Chim Organ e Industriale   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

TETRALIN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029933465     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00108-5     Document Type: Article

References (18)

1. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
2. Sakai, K.; Suemune, H. Tetrahedron. Asymmetry 1993, 4, 2109-2118.
3. Xie, Z. F.; Nakamura, I.; Suemune,H.; Sakai, K. J. Chem. Soc. Chem. Commun 1988, 966-967.
4. For the synthesis of racemic trans-2,3-dihydroxy-1,2,3,4-tetrahydronaphthalene, see: a) Collec, A.; Brienne, M. J.; Jacques, J. Bull. Soc. Chim. Fr. 1972, 336-342 (resolution with (-)camphanic acid is also described).
5. b) Tsang W. S.; Griffin, G. W.; Horning, M. G.; Stillwell W. G. J. Org. Chem. 1982, 47, 5339-5353.
6. 4 reduction of the (+)-anti-naphthalene-1,2:3,4-dioxide, in turns obtained by a multistep procedure from 1,4-naphthoquinone) see: c) Koreeda, M.; Yoshihara, M. J. Chem. Soc. Chem. Commun. 1981, 974-976.
7. Bestetti, P.; Bianchi, D.; Bosetti, A.; Di Gennaro, P.; Galli, E.; Leoni, B.; Pelizzoni, F.; Sello, G. Microbiol. Biotech., in press.
8. Examples are known where a polar substituent, as an hydroxyl group, in the allylic position has a significant influence on the direction of attack by the peroxy acid. The protected alcohol gives the trans epoxide, whilst the free alcohol affords the cis-epoxide, due to hydrogen bonding which causes an orientation favourable for cis-epoxidation. a) Berti, G. in "Topics in Stereochemistry", 1973 Vol. 7, ed. N. L. Allinger and E. L. Eliel (London: Wiley).
9. b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. T. Janssen Chim. Acta 1990, 8, 3 - 8.
10. c) Ganey, M. V.; Padykula, R. E.; Berchtold, G. A.; Braun, A. G. J.Org. Chem. 1989, 54, 2787-2793.
11. a) Takano, S.; Akiyama, M.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 1593-1596;
12. b) Shill, G.; Doerier, C.; Logeman, E.; Vetter, W. Chem. Ber. 1980, 113, 3697-3705.
13. Orsini, F.; Pelizzoni, F., Gazz. Chim. Ital. 1983, 113, 183-186.
14. Hutchins, R. O.;Taffer, I. M.; Burgoyne, W. J. Org. Chem., 1981, 46, 5214-5215.
15. a) Johnstone, R. A. W.; Wilby, A. H. Chem. Rev. 1985, 85, 129-170.
16. b) Felix, A. M., Heimer, E. P., Lambros, T. J.; Tzougraki, C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194-419
17. Fang, C.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1991, 2, 389-398.
18. 11.