Regioselective reductive ring opening of cyclic 1,2- and 1,3-benzylidene acetals

Chemistry Letters

Volumn , Issue 12, 1998, Pages 1273-1274

  Chandrasekhar, S ^a   Ravindra Reddy, Y ^a   Raji Reddy, Ch ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032268790     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1273     Document Type: Article

References (20)

1. a)T. W. Greene and P. G. M. Wuts, "Protective Groups in Organic Synthesis, 2nd ed.", Wiley, New York (1991).
2. b)P. J. Kocienski, "Protecting Groups", Thieme, Stuttgart (1994).
3. a) Gelas, J. Adv. Carbohydr. Chem. Biochem. 39, 71 (1981).
4. b)S. S. Bhattacharjee, P. A. Gorin, Can. J. Chem. 47, 1195 (1969).
5. c) A. Liptak, I. Jodal, and P. Nanasi, Carbohydr. Res. 44, 1(1975).
6. d) P. Fugedi, A. Liptak, P. Nanasi, and J. Szejtli, Carbohydr. Res. 104, 55(1982).
7. T. Mikami, H. Asano, and O. Mitsunobu, Chem. Lett. 1987, 2033.
8. M. Olikawa, W. Chi Liu, Y. Nakai, S. Koshida, K. Fukase, and S. Kusumoto, Synlett., 1996, 1179.
9. a) P. J. Garegg, H. Hulberg, and S. Wallin Carbohydr. Res. 108, 97(1982).
10. b) D.A. Horne, and A. Jordan, Tetrahedron Lett., 1978, 1357.
11. c) P. J. Garegg and H. Hultberg, Carbohydr. Res., 93, C10(1981)
12. M. P. DeNinno, J. B. Etienne, and K. C. Duplantier, Tetrahedron Lett. 36, 669 (1995).
13. a)R. Johansson, and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1984, 2371.
14. b)Y. Guindon, Y. Girard, S. Berthiaume, V. Gorys, R. Lemieux, and C. Yoakim, Can. J. Chem., 68, 897 (1990).
15. a)S. Chandrasekhar, Y. Ravindra Reddy, and C. Ramarao Synth. Commun. 27, 2251 (1997).
16. b) X. Verdaguer, S.C. Berck, and S. L. Buchwald, J. Am. Chem. Soc. 117, 12641 (1995).
17. c) E. Keinan and N. Greenspoon, J. Org. Chem., 48, 3545 (1983).
18. d) S. W. Breeden and N. J. Lawrence, Synlett. 10, 833 (1994).
19. The structures of the products were unambiguously confirmed by comparing with literature data and / or by acetylating the resulting free alcohols.
20. 2 (3×50 ml), washed with water, brine and dried over sodium sulphate. The solvent was removed under reduced pressure and the pure product was isolated by simple column chromatography (silica gel 100-200 mesh, 25: 2 hexane : ethyl acetate) in 80% yield. IICT Communication No. 3868.