Transition metal-free activation of allylic acetates toward regioselective S-allylation of thiols

Tetrahedron Letters

Volumn 51, Issue 14, 2010, Pages 1902-1905

  Saha, Amit ^a   Ranu, Brindaban C ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Allyl acetate; Regioselectivity; S Allylation; Thiols; Transition metal free

Indexed keywords

ACETIC ACID DERIVATIVE; ALIPHATIC COMPOUND; ALLYL COMPOUND; AROMATIC COMPOUND; POTASSIUM CARBONATE; THIOL; TRANSITION ELEMENT;

ALLYLATION; ARTICLE; STEREOCHEMISTRY;

EID: 77649181121     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.015     Document Type: Article

References (38)

1. Metzner P., and Thuillier A. Sulfur Reagents in Organic Synthesis (1994), Academic Press, London, U.K. p. 75
2. Grobel B.T., and Seebach D. Synthesis (1977) 357-402
3. Evans D.A., and Andrews G.C. Acc. Chem. Res. 7 (1974) 147-155
4. (d). Hegedus L.S. In: Hegedus L.S. (Ed). Transition Metals in the Synthesis of Complex Organic Molecules (1999), University Science Book, Sausalita, CA p. 245
5. Heumann A. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis vol. 1 (2004), Wiley-VCH, Weinheim, Germany 251
6. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395-422
7. Johannsen M., and Jorgensen K.A. Chem. Rev. 98 (1998) 1689-1708
8. Yatsumonji Y., Ishida Y., Tsubouchi A., and Takeda T. Org. Lett. 9 (2007) 4603-4606
9. Trost B.M., and Scanlan T.S. Tetrahedron Lett. 27 (1986) 4141-4144
10. Gais H.-J., Jagusch T., Spalthoff N., Gerhards F., Frank M., and Raabe G. Chem. Eur. J. 9 (2003) 4202-4221
11. Goux C., Lhoste P., Sinou D., and Muzart J. Sulfur Letters 18 (1994) 1-8
12. Frank M., and Gais H.-J. Tetrahedron: Asymmetry 9 (1998) 3353-3357
13. Santos S.D., Quignard F., Sinou D., and Choplin A. Topic in Catalysis 13 (2000) 311-318
14. Trost B.M., and Verhoeven T.R. J. Am. Chem. Soc. 102 (1980) 4730-4743
15. Ranu B.C., and Jana R. Adv. Synth. Catal. 347 (2005) 1811-1818
16. Salvatore R.N., Smith R.A., Nischwitz A.K., and Gavin T. Tetrahedron Lett. 46 (2005) 8931-8935
17. Vijaikumar S., and Pitchumani K. J. Mol. Catal. A: Chem. 217 (2004) 117-120
18. Varma R.S., and Reddy T.I. Chem. Commun. (1997) 621-622
19. Juslen C., and Enkvist T. Acta Chem. Scand. 12 (1958) 287-297
20. Arnau N., Moreno-Mafias M., and Pleixats R. Tetrahedron 47 (1993) 11019-11028
21. Kondo T., and Mitsudo T. Chem. Rev. 100 (2000) 3205-3220
22. Goux C., Lhoste P., and Sinou D. Tetrahedron 50 (1994) 10321-10330
23. Komine N., Sako A., Hirahara S.-Y., Hirano M., and Komiya S. Chem. Lett. 34 (2005) 246-247
24. Zaitsev A.B., Caldwell H.F., Pregosin P.S., and Veiros L.F. Chem. Eur. J. 15 (2009) 6468-6477
25. Kondo T., Morisaki Y., Uenoyama S.-Y., Wada K., and Mitsudo T.-A. J. Am. Chem. Soc. 121 (1999) 8657-8658
26. Zhang X., Rao W., Wai P., and Chan H. Synlett (2008) 2204-2208
27. Sanz R., Martinez A., Miguel D., Alvarez-Gutierrez J.M., and Rodriguez F. Adv. Synth. Catal. 348 (2006) 1841-1845
28. Tamura S., Shiomi A., Kaneko M., Ye Y., Yoshida M., Yoshikawa M., Kimura T., Kobayashi M., and Murakami M. Bioorg. Med. Chem. Lett. 19 (2009) 2555-2557
29. Kimura M., Horino Y., Mori M., and Tamaru Y. Chem. Eur. J. 13 (2007) 9686-9702
30. de Cadenet K.G., Rumin R., Petillon F.Y., Yufit D.S., and Muir K.W. Eur. J. Inorg. Chem. (2002) 639-657
31. 2 = 1.1 Hz), 3.79 (3H, s), 5.99-6.09 (1H, m), 6.37
32. Van Otterlo W.A.L., Morgans G.L., Khanye S.D., Aderibigbe B.A.A., Michael J.P., and Billing D.G. Tetrahedron Lett. 45 (2004) 9171-9175
33. Tang R.-Y., Zhong P., and Lin Q.-L. Synthesis (2007) 85-97
34. Atkinson R.S., and Awad S.B. Chem. Commun. (1975) 651-652
35. Saxena A.K., Kumar A., and Mozumdar S. Appl. Catal., A: General 317 (2007) 210-215
36. Lissel M., Schmidt S., and Neumann B. Synthesis (1986) 382-383
37. Nayak S.K., Thijs L., and Zwanenburg B. Tetrahedron Lett. 40 (1999) 981-984
38. Dai C., Zhu S., Yu Z., and Cohen T. J. Am. Chem. Soc. 123 (2001) 30-34