An efficient synthesis and resolution of (±)-cis,cis-spiro[4.4]nonane- 1,6-diol

Synthetic Communications

Volumn 29, Issue 21, 1999, Pages 3829-3840

  Nieman, James A ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REDUCTION; SYNTHESIS;

EID: 0032836899     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908086023     Document Type: Article

References (24)

1. Nieman, J.A. and Keay, B.A. Tetrahedron: Asymmetry 1993, 4, 1973.
2. For previous syntheses and resolutions of 4, see: a) Cram, D.J.; Steinberg, H. J. Am. Chem. Soc. 1954, 76, 2754.
3. b) Hardegger, E.; Maeder, E.; Semarne, H.M.; Cram, D. J. Am. Chem. Soc. 1959, 81, 2729.
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7. f) Carruthers, W.; Orridge, A. J. Chem.Soc., Perkin Trans. 1 1977, 2411.
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11. j) Suemune, H.; Maeda, K.; Kato, K.; Sakai, K. . J. Chem. Soc., Perkin Trans. 1. 1994, 3441.
12. For the synthesis and resolution of a related spirobiindane-diol, see: Nieman, J.A., Keay, B.A. Tetrahedron: Asymm. 1995, 6, 1575.
13. Nieman, J.A.; Keay, B.A.; Kubicki, M.; Yang, D.; Rauk, A.; Tsankov, D. and Wieser, H. J. Org. Chem. 1995, 60, 1918.
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16. a) Nieman, J.A. and Keay, B.A. Tetrahedron: Asymmetry 1996, 7, 3521.
17. b) Keay, B.A.; Maddaford, S.P.; Cristofoli, W.A.; Andersen, N.G.; Passafaro, M.S.; Wilson, N.S.; Nieman, J.A. Can. J. Chem. 1997, 75, 1163.
18. Chan, A.S.C.; Hu, W.; Pai, C.-C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R. and Deng, J. J. Am. Chem.Soc. 1997, 119, 9570.
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20. (b) Srivastava, N.; Mital, A. and Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493.
21. In the past year, nine different research groups around the globe have written or emailed us regarding the details on the synthesis and resolution of diol 4.
22. For the assignment of absolute stereochemistry to the spiro carbon atom, it is treated as a centre of chirality (formally a (ab)C(ba) system), not as an axis of chirality. For more information, see: Cahn, R.S.; Ingol, C.: Prelog, V. Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
23. Bachmann, W.E.; Struve, W.S. J. Am. Chem. Soc. 1941, 63, 2589.
24. Kabuto, K.; Yasuchara, F.; Yamaguchi, S. Tetrahedron Lett. 1984, 25, 5801.