Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones

Chemistry Letters

Volumn , Issue 1, 1996, Pages 67-68

  Jiang, Shende ^a   Singh, Gurdial ^a   Wightman, Richard H ^b  

^a TEESSIDE UNIVERSITY   (United Kingdom)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030554322     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.67     Document Type: Article

References (12)

1. For a review, see: R. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984).
2. For the nomenclature, see: S. Masamune, S. A. Ali, D. L. Snitman, and D. S. Garvey, Angew. Chem., Int. Ed. Engl., 19, 557 (1980).
3. a) J. G. Buchanan, K. A. MacLean, R. H. Wightman, and H. Paulsen, J. Chem. Soc., Perkin Trans, 1, 1985, 1463.
4. b) M. Kinoshita, M. Arai, K. Tomooka, and M. Nakata, Tetrahedron Lett., 27, 1811 (1986).
5. c) T. Mukaiyama, K. Suzuki, T. Yamada, and F. Tabusa, Tetrahedron, 46, 265 (1990).
6. d) B. Mekki, G. Singh, and R. H. Wightman, Tetrahedron Lett. 32, 5143 (1991).
7. a) M. Cherest, H. Felkin, and N. Prudent, Tetrahedron Lett., 1968, 2199.
8. b) N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1, 61 (1977).
9. For a couple of exceptional cases where the syn-products were mainly obtained, see: a) F. Sato, Y. Kobayashi, O. Takahashi, T. Chiba, Y. Takeda, and M. Kusakabe, J. Chem. Soc., Chem. Commun., 1985, 1636.
10. b) see also Ref. 3d.
11. N. Cohen, B. L. Banner, R. J. Lopresti, F. Wong, M. Rosenberger, Y. Y. Liu, E. Thom, and A. A. Liebman, J. Am. Chem. Soc., 105, 3661 (1983).
12. 3). Its mp was previously reported as 68 °C, see: J. A. Piccirilli, T. Krauch, L. J. MacPherson, and S. A. Benner, Helv. Chim. Acta, 74, 397 (1991).