A new strategy for chemoselective O-acylation of β-mercapto alcohols via alkylsilyl and stannyl protection

Tetrahedron Letters

Volumn 50, Issue 4, 2009, Pages 480-483

  Maheswara, Muchchintala ^a   Kim, Mirae ^a   Yun, Sun Ju ^a   Ju, Jung Jin ^b   Do, Jung Yun ^a  

^a Pusan National University   (South Korea)

^b Electronics and Telecommunications Research Institute (ETRI)   (South Korea)

Author keywords

Mercapto alcohol; Alkoxy tin; Chemoselective acrylation; O Acrylation

Indexed keywords

MERCAPTOETHANOL;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMOSENSITIVITY; COLUMN CHROMATOGRAPHY; DEPROTECTION REACTION;

EID: 57149140982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.047     Document Type: Article

References (27)

1. Greene T.W., and Wuts P.G.M. Protective groups in organic synthesis. 3rd ed. (1999), John Wiley and Sons, New York
2. Hajjar A.B., Nicks P.F., and Knowles C.J. Biotechnol. Lett. 12 (1990) 825
3. Kang Y., and Taton T.A. Angew. Chem., Int. Ed. Engl. 44 (2005) 409
4. Li Z., Jin R., Mirkin C.A., and Letsinger R.L. Nucleic Acids Res. 30 (2002) 1558
5. Becker D., Summerfield S., Gillich S., and Sevilla M.D. Int. J. Radiat. Biol. 65 (1994) 537
6. Biaglow J.E., Varnes M.E., Clark E.P., and Epp E.R. Radiat. Res. 95 (1983) 437
7. Sigdestad C.P., Connor A.M., and Sims C.S. Int. J. Radiat. Oncol. Biol. Phys. 22 (1992) 807
8. Yuhas J.M. Cancer Res. 40 (1980) 1519
9. Weiss J.F., and Simic M.G. Pharmacol. Ther. 39 (1988) 1
10. Kilambi H., Reddy S.K., Schneidewind L., Stansbury J.W., and Bowman C.N. Polymer 48 (2007) 2014
11. Hunks W.J., Jennings M.C., and Puddephatt R.J. Chem. Commun. (2002) 1834
12. Selliger H., and Gortz H.H. Synth.Commun. 10 (1980) 175
13. Kumar P., Pandey R.K., Bodas M.S., Dagade S.P., Dongare M.K., and Ramaswamy A.V. J. Mol. Catal. A: Chem. 181 (2002) 207
14. Bruice T.C. In: Kharasch N. (Ed). Organic Sulfur Compounds Vol. 1 (1961), Springer, London 421
15. Shelkov R., Nahmany M., and Melman A. Org. Biomol. Chem. 2 (2004) 397
16. Nahmany M., and Melman A. Synthesis (2006) 2841
17. Baldessari A., Iglesias L.E., and Gros E.G. J. Chem. Res. (S) (1992) 204
18. Baldessari A., Iglesias L.E., and Gros E.G. Biotechnol. Lett. 16 (1994) 479
19. Wang Y.F., and Wong C.H. J. Org. Chem. 53 (1988) 3127
20. Colombo D., Ronchetti F., Scala A., and Toma L. J. Carbohydr. Chem. 11 (1992) 89
21. Panza L., Luisetti M., Crociati E., and Riva S. J. Carbohydr. Chem. 12 (1993) 125
22. Kanerva L., Rahiala K., and Vanttinen E. J. Chem. Soc. Perkin Trans. 1 (1992) 1759
23. Izumi T., and Fuyaka K. Bull. Chem. Soc. Jpn. 66 (1993) 1216
24. The reason of the opposite selectivity is not clear. The possibility of intramolecular acyl rearrangement was excluded because isolated two products of O-acetyl and S-acetyl did not interconvert in methylene chloride containing triethylamine.
25. Lalancette J.M., and Freche A. Can. J. Chem. 49 (1971) 4047
26. Djerassi C., Gorman M., Markley F.X., and Oldenburg E.B. J. Am. Chem. Soc. 77 (1955) 568
27. 3, 300 MHz): δ 2.33 (s, 3H), 7.15-7.24 (m, 2H), 7.30 (d, 1H, J = 7.8 Hz), 7.59 (dd, 1H, J = 7.8 Hz).