Studies on the diastereoselective alkylation reaction employing isomannide and isosorbide as chiral auxiliaries

Chinese Chemical Letters

Volumn 9, Issue 4, 1998, Pages 325-328

  Wang, Jian Qiang ^a   Xu, Ming Hua ^a   Zhong, Min ^a   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Diastereoselective alkylation; Isomannide; Isosorbide

Indexed keywords

EID: 0032271330     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. P. Cintas, Tetrahedron ,1991, 47, 6079.
2. a) L. F. Wiggins, Advances in Carbohydrate Chem., 1950, 5, 191.
3. b) A. C. Cope, T. Y. Shen, J. Am. Chem. Soc, 1956, 3177.
4. c) T. G. Archibald, K. Baum, Synthetic Commun., 1989, 19, 1493.
5. d) J. Kuszmann, G. Medgyes, Carbohydrate Research, 1980, 85, 259.
6. e) A. P. Arya, India J. Chem., Sect. B, 1978, 16B, 153.
7. f) J. Thiem, F. Bachmann, Makromol. Chem., 1991, 192, 2163.
8. g) P. Stoss, S. Erhardt, Bioorganic & Medicinal Chem. Lett., 1991, 1, 629 and references cited therein.
9. a) A. Hirao, H. Mochizuki, S. Nakahama, N. Yamazaki, J. Org. Chem., 1979, 44, 1720.
10. b) H. H. Zoorob, Egypt. J. Chem., 1986, 29, 333.
11. c) R. Tamion, F. Marsais, P. Rinereau, G. Queguiner, D. Abenhaim, A. Loupy, L. Munnier, Tetrahedron: Asymmetry, 1993, 4, 1879.
12. d) R. Tamion, F. Marsais, P. Ribereau, G. Queguiner, Tetrahedron: Asymmetry, 1993, 4, 2415.
13. e) V. Nair, J. Prabahakaram, J. Chem. Soc., Perkin Trans., 1996, 1, 593.
14. f) A. Loupy, D. Monteux, Tetrahedron Lett., 1996, 37, 7023.
15. a) L. F. Wiggins, J. Chem. Soc., 1945, 4.
16. b) R. Montgomery, L. F. Wiggins, J. Chem. Soc., 1946, 390.
17. 6), for S configuration: D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737}. The alcohol 13 was obtained by the following reductive cleavage: 5,6,10,11,12 Equation Presented
18. a) D. A. Evans, J. M. Takacs, Tetrahedron Lett., 1980, 21, 4233.
19. b) Y. Kawanami, Y. Ito, T. Kitagawa, Y. Tannguchi, T. Katsuki, M. Yamaguchi, Tetrahedron Lett., (1984), 25, 857.
20. c) W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett., 1989, 30, 5603.
21. d) W. Oppolzer, I. Rodringuez, C. Starkemann, E. Walther, Tetrahedron Lett., 1990, 31, 5019.
22. -1. All of these data have been submitted to CCL editorial department.