Acid-catalyzed regioselective sulfetherification of alkenols and stereoselective rearrangement of tetrahydrofuran to tetrahydropyran

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1650-1653

  Wang, Haining ^a   Huang, Deshun ^a   Cheng, Donghao ^a   Li, Lijun ^a   Shi, Yian ^a,b  

^a INSTITUTE OF CHEMISTRY   (China)

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953193809     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200127n     Document Type: Article

References (29)

1. Shi, Y. Acc. Chem. Res. 2004, 37, 488
2. Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762
3. For a leading review on electrophilic sulfur additions to olefins, see: Rayner, C. M. In Organosulfur Chemistry: Synthetic Aspects; Page, P., Ed.; Academic Press: London, 1995; p 89.
4. For a leading review on sulfenamides, see: Craine, L.; Raban, M. Chem. Rev. 1989, 89, 689
5. For leading references on acid-promoted addition of RS or RSe to olefins with RS-N or RSe-N reagents, see: Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704
6. Caserio, M. C.; Kim, J. K. J. Am. Chem. Soc. 1982, 104, 3231
7. Brownbridge, P. Tetrahedron Lett. 1984, 25, 3759
8. Benati, L.; Montevecchi, P. C.; Spagnolo, P. Tetrahedron 1986, 42, 1145
9. Brownbridge, P. J. Chem. Soc., Chem. Commun. 1987, 1280
10. For leading references on acid-promoted addition of RS to olefins with RSSR or RSOR reagents, see: Trost, B. M.; Ochiai, M.; McDougal, P. G. J. Am. Chem. Soc. 1978, 100, 7103
11. Edstrom, E. D.; Livinghouse, T. J. Am. Chem. Soc. 1986, 108, 1334
12. Ito, Y.; Ogawa, T. Tetrahedron Lett. 1987, 28, 2723
13. Taniguchi, N. J. Org. Chem. 2006, 71, 7874
14. Yamagiwa, N.; Suto, Y.; Torisawa, Y. Bioorg. Med. Chem. Lett. 2007, 17, 6197
15. For leading references on Lewis base promoted addition of RSe to olefins with RSe-N reagents, see: Denmark, S. E.; Collins, W. R. Org. Lett. 2007, 9, 3801
16. Denmark, S. E.; Kalyani, D.; Collins, W. R. J. Am. Chem. Soc. 2010, 132, 15752
17. For cis -5-octen-1-ol, only 6- exo product was detected with both TsOH and TfOH.
18. For leading references on tetrahydofuran rearrangement to tetrahydropyran via thiiranium and seleniranium, see: Gruttadauria, M.; Lo Meo, P.; Noto, R. Tetrahedron 2001, 57, 1819
19. Gruttadauria, M.; Noto, R. J. Heterocycl. Chem. 2001, 38, 765
20. Fox, D. J.; House, D.; Warren, S. Angew. Chem., Int. Ed. 2002, 41, 2462
21. Gruttadauria, M.; Aprile, C.; Noto, R. Tetrahedron Lett. 2002, 43, 1669
22. Aprile, C.; Gruttadauria, M.; Amato, M. E.; D'Anna, F.; Lo Meo, P.; Riela, S.; Noto, R. Tetrahedron 2003, 59, 2241
23. For leading references on enantiomerically enriched thiiranium ions, see: Blanchette, H. S.; Branchaud, B. P. Tetrahedron Lett. 2002, 43, 351
24. Denmark, S. E.; Vogler, T. Chem.-Eur. J. 2009, 15, 11737
25. For a leading reference on studies of stability of thiiranium ions, see: Denmark, S. E.; Collins, W. R.; Cullen, M. D. J. Am. Chem. Soc. 2009, 131, 3490
26. For a leading reference on chiral sulfur reagent-mediated reactions, see: Bürgler, F. W.; Fragale, G.; Wirth, T. ARKIVOC 2007, 21
27. For leading reviews on chiral selenium reagent-mediated reactions, see: Wirth, T. Angew. Chem., Int. Ed. 2000, 39, 3740
28. Freudendahl, D. M.; Shahzad, S. A.; Wirth, T. Eur. J. Org. Chem. 2009, 1649
29. For a reference on chiral Lewis base catalyzed selenoetherification, see ref 7b.