1,1'-Spirobiindane-7,7'-diol: A novel, C2-symmetric chiral ligand

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 125-131

  Birman, Vladimir B ^a   Rheingold, Arnold L ^b   Lam, Kin Chung ^b  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' SPIROBIINDANE 7,7' DIOL; ANISALDEHYDE; CARBOXYLIC ACID DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033556676     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00481-9     Document Type: Article

References (23)

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2. (a) BINAP: Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.
3. (b) BINAPO: Grubbs, R. H.; De Vries, R. A. Tetrahedron Lett. 1977, 1879.
4. 2-symmetry in asymmetric synthesis, see: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
5. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p. 1138.
6. (a) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C.-P. J. Am. Chem. Soc. 1997, 119, 9570.
7. (b) Srivastava, N.; Mital, A.; Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493.
8. (c) Original preparation and resolution: Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1954, 76, 2753. Hardeggar, E.; Maeder, E.; Semarne, H. M.; Cram, D. J. J. Am. Chem. Soc. 1959, 81, 2729.
9. (c) Original preparation and resolution: Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1954, 76, 2753. Hardeggar, E.; Maeder, E.; Semarne, H. M.; Cram, D. J. J. Am. Chem. Soc. 1959, 81, 2729.
10. Prelog, V.; Mutak, S. Helv. Chim. Acta 1983, 66, 2274.
11. (a) Preparation of both enantiomers of the parent compound: Brewster, J. H.; Prudence, R. T. J. Am. Chem. Soc. 1973, 95, 1217. Hill, R. K.; Cullison, D. A. J. Am. Chem. Soc. 1973, 95, 1229.
12. (a) Preparation of both enantiomers of the parent compound: Brewster, J. H.; Prudence, R. T. J. Am. Chem. Soc. 1973, 95, 1217. Hill, R. K.; Cullison, D. A. J. Am. Chem. Soc. 1973, 95, 1229.
13. (b) Baker, W. J. Chem. Soc. 1934, 1678.
14. (c) Hagishita, S.; Kuriyama, K.; Hayashi, M.; Nakano, Y.; Shingu, K.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 496.
15. (d) Hoeve, W. T.; Wynberg, H. J. Org. Chem. 1980, 45, 2930.
16. (e) Tanaka, T.; Miyaguchi, M.; Mochisuki, R. K.; Tanaka, S.; Okamoto, M.; Kitajima, Y.; Miyazaki, T. Heterocycles 1987, 25, 463.
17. Kazlauskas, R. J. J. Am. Chem. Soc. 1989, 111, 4953.
18. Conard, C. R.; Dolliver, M. A. Org. Synth., Coll. Vol. II, 167.
19. Although preparation of 1,5-bis-m-anisyl-3-pentanone via this route has been described, 7c difficulties were encountered in repeating the condensation step according to the published procedure. In addition, reduction with Raney nickel as a catalyst proved to be more convenient than with Pd/C, causing very little over-reduction to the alcohol and thus obviating the need for purification.
20. 4, PhH, reflux) 7e afforded, at best, 39% yield.
21. Gong, B.-Q.; Chen, W.-Y.; Hu, B.-F. J. Org. Chem. 1991, 56, 423.
22. Although spiranes possess axial symmetry, for purposes of nomenclature they are treated as having a chiral center. 4 Configurationally, (S)-(-)-SPINOL corresponds to (R)-(+)-BINOL.
23. Correspondence regarding the X-ray data should be addressed to Professor Arnold L. Rheingold, University of Delaware.