Reductive cleavage of benzyl ethers with lithium naphthalenide. A convenient method for debenzylation

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2253-2256

  Liu, Hsing Jang ^a   Yip, Judy ^a   Shia, Kak Shan ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031592554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00345-6     Document Type: Article

References (11)

1. 1. Liu, H. J.; Shia, K. S.; Han, Y.; Wang, Y. Synlett 1995, 545-546.
2. 2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991; pp. 47-53.
3. 3. Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972-989.
4. 4. Padron, J. I.; Vazquez, J. T. Tetrahedron: Asymmetry 1995, 6, 857-858.
5. 5. Stinnett, J. W.; Vora, M. M.; Holy, N. L. Tetrahedron Lett. 1974, 3821-3824.
6. 6. For previous examples of using the enolate as a protecting group, see references 1, 7 and 8.
7. 7. Coates, R.M.; Shaw, J.E. J. Org. Chem. 1970, 92, 5657-5664.
8. 8. Goldsmith, D.J.; Lewis, A.J.; Still, W.C., Jr. Tetrahedron Lett. 1973, 4807-4810.
9. 9. Alternatively, a stock solution of lithium naphthalenide prepared in the same manner could be conveniently used. The stock solution was found to retain virtually the same reactivity after storage in a fridge at ca. -4°C under argon atmosphere for more than a month.
10. 11
11. 11. Azzena, U.; Demartis, S.; Melloni, G. J. Org. Chem. 1996, 61, 4913-4919.