Indium triflate mediated acetalization of aldehydes and ketones

Tetrahedron Letters

Volumn 47, Issue 52, 2006, Pages 9317-9319

  Smith, Brendan M ^a   Graham, Andrew E ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

Acetalization; Indium triflate

Indexed keywords

ACETAL; ALDEHYDE DERIVATIVE; INDIUM TRIFLATE; KETONE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; REACTION TIME; ROOM TEMPERATURE;

EID: 33751176464     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.111     Document Type: Article

References (17)

1. Kocienski P.J. Protecting Groups (2003), Thieme, New York
2. Wenkert E., and Goodwin T.E. Synth. Commun. 7 (1977) 409-415
3. Torok D.S., Figueroa J.J., and Scott W.J. J. Org. Chem. 58 (1993) 7274-7276
4. Lu T.-J., Yang J.-F., and Sheu L.-J. J. Org. Chem. 60 (1995) 2931-2934
5. Yu M., and Pagenkopf B.L. Tetrahedron 59 (2003) 2765-2771
6. Gemal A.L., and Luche J.H. J. Org. Chem. 44 (1979) 4187-4189
7. Ishihara K., Karumi Y., Kubota M., and Yamamoto H. Synlett (1996) 839-841
8. Clerici A., Pastori N., and Porta O. Tetrahedron 54 (1998) 15679-15690
9. Firouzabadi H., Iranpoor N., and Karimi B. Synlett (1999) 321-323
10. Leonard N.M., Oswald M.C., Freiberg D.A., Nattier B.A., Smith R.C., and Mohan R.S. J. Org. Chem. 67 (2002) 5202-5207
11. Kumar R., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 8319-8323
12. Fringuelli F., Piermatti O., Pizzo F., and Vaccaro L. Curr. Org. Chem. 7 (2003) 1661-1689
13. Yin L.A., Zhang Z.H., Wang Y.M., and Pang M.L. Synlett (2004) 1727-1730
14. Ceschi M.A., de Araujo Felix L., and Peppe C. Tetrahedron Lett. 41 (2000) 9695-9699
15. Ranu B.C., Jana R., and Samanta S. Adv. Synth. Catal. 346 (2004) 446-450
16. Indium trichloride has been reported to be a poor catalyst for acetal formation in the absence of trimethyl orthoformate;. Kim Y.-J., and Varma R.S. Tetrahedron Lett. 46 (2005) 7447-7449
17. An aqueous work-up of the reaction mixture led to a rapid and complete hydrolysis of the acetal back to the corresponding carbonyl compound.