Trifluoroacetic acid catalyzed tetrahydropyranylation of alcohols and phenols and direct conversion of THP ethers into acetates

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 51, Issue 2, 2012, Pages 356-361

  Bodipati, Naganjaneyulu ^a   Palla, Srinivasa Rao ^a   Peddinti, Rama Krishna ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

Author keywords

Acetates; Alcohols; Phenols; Tetrahydropyranylation; THP ethers; Trifluoroacetic acid

Indexed keywords

EID: 84857320445     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Greene T W & Wuts P G M, Protective Groups in Organic Synthesis, 2nd edn (John Wiley and Sons, New York), 1999.
2. (a) Corey E J, Niwa H & Knolle J, J Am Chem Soc, 100, 1978, 1942;
3. (b) Bernady K F, Floyd M B, Poletto J F & Weiss M J, J Org Chem, 44, 1979, 1438;
4. (c) Lin H C, Du W P, Chang C C & Lin C H, Tetrahedron Lett, 46, 2005, 5071.
5. Alper H & Dinkes L, Synthesis, 1972, 81.
6. Ranu B C & Saha M, J Org Chem, 59, 1994, 8269.
7. Naik S, Gopinath R & Patel B K, Tetrahedron Lett, 42, 2001, 7679.
8. Miyashita M, Yoshikoshi A & Grieco P A, J Org Chem, 42, 1977, 3772.
9. Hon Y S, Lee C F, Chen R J & Szu P H, Tetrahedron, 57, 2001, 5991.
10. Namboodiri V V & Varma R S, Tetrahedron Lett, 43, 2002, 1143.
11. Mineno T, Tetrahedron Lett, 43, 2002, 7975.
12. Stephens J R, Butler P L, Clow C H, Oswald M C, Smith R C & Mohan R S, Eur J Org Chem, 2003, 3827.
13. Karimi B & Maletki J, Tetrahedron Lett, 43, 2002, 5353.
14. Namboodiri V V & Verma R S, Chem Commun, 2002, 342.
15. Yadav J S, Reddy B V S & Gnaneshwar D, New J Chem, 27, 2003, 202.
16. Khan A T, Mondal E, Boah B M & Ghosh S, Eur J Org Chem, 2003, 4113.
17. Khan A T, Choudary L H & Ghosh S, Tetrahedron Lett, 45, 2004, 7891.
18. Pachamuthu K & Vankar Y D, J Org Chem, 66, 2001, 7511.
19. Khan A T, Ghosh S & Choudhury L H, Eur J Org Chem, 2005, 4891.
20. Oates R P & Jones P B, J Org Chem, 73, 2008, 4743.
21. Wang M, Song Z G, Gong H & Jiang H, Monatsh Chem, 140, 2009, 177.
22. Ganem B & Small Jr V R, J Org Chem, 39, 1974, 3728.
23. Schwarz M & Waters R M, Synthesis, 1972, 567.
24. Chandrasekhar S, Ramachandar T, Reddy M V & Takhi M, J Org Chem, 65, 2000, 4729.
25. Ranu B C & Hajra A, J Chem Soc Perkin Trans I, 2001, 355.
26. Oriyama T, Kobayashi K, Suzuki T & Oda M, Green Chem, 4, 2002, 30.
27. Chandra K L, Saravanan P & Singh V K, Tetrahedron Lett, 42, 2001, 5309.
28. Heravi M M, Behbahani F K, Shoar R H & Oskooie H A, J Mol Catal, 244, 2006, 8 and references cited therein.
29. Das B, Reddy M R, Reddy K R, Ramu R & Thirupathi P, J Mol Catal, 248, 2006, 185.
30. Hoyer S & Laszlo P, Synthesis, 1986, 655.