Studies on the hydrogenolysis of benzyl ethers

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5815-5818

  Llàcer, Enric ^a   Romea, Pedro ^a   Urpí, Fèlix ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Benzyl ether; Protecting groups; Selective hydrogenolysis

Indexed keywords

BENZYL DERIVATIVE; BENZYL ETHER; ETHER; NATURAL PRODUCT; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; HYDROGENOLYSIS;

EID: 33745604252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.109     Document Type: Article

References (22)

1. Greene T.W., and Wuts R.G.M. Protective Groups in Organic Synthesis (1999), John Wiley & Sons, New York
2. Kocienski P.J. Protecting Groups (1994), Thieme, Stuttgart
3. Surprisingly and to the best of our knowledge, this problem has been rarely identified. For instance, see:. Bolitt V., Mioskowski C., Kollah R.O., Manna S., Rajapaksa D., and Falck J.R. J. Am. Chem. Soc. 113 (1991) 6320-6321
4. Jennings M.P., and Clemens R.T. Tetrahedron Lett. 46 (2005) 2021-2024
5. For a recent review on ether dealkylation, see:. Weissman S.A., and Zewge D. Tetrahedron 61 (2005) 7833-7863
6. For a recent evaluation of selectivity on the hydrogenolysis of benzyl amines, see:. Kanai M., Yasumoto M., Kuriyama Y., Inomiya K., Katsuhara Y., and Higashiyama I. Org. Lett. 5 (2003) 1007-1010
7. For a classical study on the selective deprotection of benzyl-like protecting groups for alcohols, see:. Horita K., Yoshioka T., Tanaka T., Oikawa Y., and Yonemitsu O. Tetrahedron 42 (1986) 3021-3028
8. For a recent survey on debenzylation conditions, see:. Trost B.M., Wrobleski S.T., Chisholm J.D., Harrington P.E., and Jung M. J. Am. Chem. Soc. 127 (2005) 13589-13597
9. For other O-Bn-like protecting groups recently reported, see:. Falck J.R., Barma D.K., Baati R., and Mioskowski C. Angew. Chem., Int. Ed. 40 (2001) 1281-1283
10. Sharma G.V.M., and Rakesh. Tetrahedron Lett. 42 (2001) 5571-5573
11. See the following communication. Tetrahedron Lett. 2006, 47, doi:10.1016/j.tetlet.2006.05.187.
12. For previous reports on hydrogenolysis of debromoaplysiatoxin derivatives and oscillatoxin D, see:. Park P.-u., Broka C.A., Johnson B.F., and Kishi Y. J. Am. Chem. Soc. 109 (1987) 6205-6207
13. Toshima H., Suzuki T., Nishiyama S., and Yamamura S. Tetrahedron Lett. 30 (1989) 6725-6728
14. Toshima H., Goto T., and Ichihara A. Tetrahedron Lett. 36 (1995) 3373-3374
15. Methyl ether at C15 could be considered as methanol protected with a complex benzyl-like group.
16. 2O has been previously reported:. Hawker S., Bhatti M.A., and Griffin K.G. Chim. Oggi 10 (1992) 49-51
17. See also:. Perosa A., Tundo P., and Zinovyev S. Green Chem. 4 (2002) 492-494
18. Other reductive methodologies (Pd-mediated transfer hydrogenation or LDDP) were also tested ineffectively.
19. For a successful application of Ra Ni to the cleavage of C20 benzyl ether in a late step of the synthesis of oscillatoxin D, see Ref. 9c.
20. 3 afforded quantitatively the corresponding cyclohexylmethyl ether.{A figure is presented}
21. 3 can produce partial aromatic ring reduction:. Oikawa Y., Tanaka T., Horita K., and Yonemitsu O. Tetrahedron Lett. 25 (1984) 5397-5400
22. Selective Pd/C-mediated hydrogenolysis of a benzyl ester in the presence of an aromatic benzyl ether has been reported:. Sajiki H., Hattori K., and Hirota K. J. Org. Chem. 63 (1998) 7990-7992