Efficient tetrahydropyranyl and tetrahydrofuranyl protection/deprotection of alcohols and phenols with Al(OTf)3 as catalyst

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4573-4576

  Williams, D Bradley G ^a   Simelane, Sandile B ^a   Lawton, Michelle ^a   Kinfe, Henok H ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

Alcohol protection; Aluminium triflate; Tetrahydrofuranylation; Tetrahydropyranylation

Indexed keywords

2,2' [2 BUTYNE 1,4 DIYLBIS(OXY)]BIS(TETRAHYDRO 2H PYRAN); 2,2' [2 BUTYNE 1,4 DIYLBIS(OXY)]BIS(TETRAHYDROFUAN); ALCOHOL DERIVATIVE; METHYL 5 (TETRAHYDRO 2H PYRAN 2 YL) (2,3 O METHYLETHYLIDENE) BETA D RIBOFURANOSIDE; METHYL 5 (TETRAHYDROFURAN 2 YL) (2,3 O METHYLETHYLIDENE) B D RIBOFURANOSIDE; PHENOL DERIVATIVE; PYRAN DERIVATIVE; TETRAHYDRO 2 (1 NAPHTHALENYLOXY) 2H PYRAN; TETRAHYDRO 2 (1 PHENYLETHOXY) 2H PYRAN; TETRAHYDRO 2 (2 NAPHTHALENYLOXY) 2H PYRAN; TETRAHYDRO 2 (2 PHENYLETHOXY) 2H PYRAN; TETRAHYDRO 2 (2 PROPYN 1 YLOXY) FURAN; TETRAHYDRO 2 (2 PROPYN 1YLOXY) 2H PYRAN; TETRAHYDRO 2 (3 METHYLPHENOXY) 2H PYRAN; TETRAHYDRO 2 (4 BROMOPHENOXY) 2H PYRAN; TETRAHYDRO 2 (PHENYLMETHOXY) 2H PYRAN; TETRAHYDRO 2 (PHENYLMETHOXY) FURAN; TETRAHYDRO 2 [((1R,2S,5R) 5 METHYL 2 (1 METHYLETHYL)CYCLO HEXYL)OXY] 2H PYRAN; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROFURANYL; TETRAHYDROPYRANYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; PRIORITY JOURNAL; PROTECTION;

EID: 77953122765     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.053     Document Type: Article

References (25)

1. Wuts P.G.W., and Greene T.W. Protective Groups in Organic Synthesis. 4th ed. (2007), Wiley, New Jersey, NJ Chapters 2-3
2. Hon Y.-S., and Lee C.-F. Tetrahedron Lett. 40 (1999) 2389
3. Cheung M.-K., Douglas N.L., Hinzen B., Ley S.V., and Pannecoucke X. Synlett (1997) 257
4. Stephens J.R., Butler P.L., Clow C.H., Oswald M.C., Smith R.C., and Mohan R.S. Eur. J. Org. Chem. 20 (2003) 3827
5. Van Boom J.H., Herschied J.D.M., and Reese C.B. Synthesis (1973) 169
6. Bongini A., Cardillo G., Orena M., and Sandri S. Synthesis (1979) 618
7. Yu B., and Hui Y. Synth. Commun. 25 (1995) 2037
8. Baati R., Valleix A., Mioskowski C., Barma D.K., and Falk J.R. Org. Lett. 2 (2000) 485
9. Maione A.M., and Romeo A. Synthesis (1987) 250
10. Masahito O., and Takuya S. Tetrahedron Lett. 45 (2004) 3557
11. Kamal A., Naseer M., Khan A., Srikath Y.V., and Reddy K.S. Can. J. Chem. 86 (2008) 1099
12. Williams D.B.G., and Lawton M.L. Tetrahedron Lett. 47 (2006) 6557
13. Williams D.B.G., and Lawton M.L. Org. Biomol. Chem. 3 (2005) 3269
14. Williams D.B.G., and Lawton M.L. Green Chem. 10 (2008) 914
15. Williams D.B.G., Shaw M.L., Green M.J., and Holzapfel C.W. Angew. Chem., Int. Ed. 47 (2008) 560
16. Harcken C., and Bruckner R. New J. Chem. 25 (2001) 40
17. Khan S.T., Parvin T., and Choudhury L.H. Synthesis 15 (2006) 2497
18. Kavala V., Samal A.K., and Patel B.K. ARKIVOC i (2005) 20
19. Kumar B., Aga B.A., and Mukherjee D. Tetrahedron Lett. 50 (2009) 6236
20. Watahiki T., Kikumoto H., Matsuzaki M., Suzuki T., and Oriyama T. Bull. Chem. Soc. Jpn. 75 (2002) 367 The compound was prepared but incomplete data are given
21. Khan S.T., Ghosh S., and Choudhury L.H. Eur. J. Org. Chem. (2005) 4891
22. Cha K.H., Kang T.W., Lee H.-W., Kim E.-N., Choi N.-H., Kim J.-W., and Hong C.I. Synth. Commun. 28 (1998) 2131
23. Tayama E., and Isaka W. Org. Lett. 8 (2006) 5437
24. Alper H., and Dinkes L. Synthesis (1972) 81
25. Yadav J.S., Subba Reddy B.V., and Gnaneshwar D. New J. Chem. (2003) 202