Practical synthesis of N -Boc- and N -Cbz-α-amido stannanes from α-amido sulfones using TMSSnBu3 and CsF

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2354-2357

  Mita, Tsuyoshi ^a   Higuchi, Yuki ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CESIUM; CESIUM FLUORIDE; FLUORIDE; IMINE; ORGANOTIN COMPOUND; STANNANE; SULFONE; TIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINES; CESIUM; FLUORIDES; IMINES; MOLECULAR STRUCTURE; ORGANOTIN COMPOUNDS; SULFONES; TIN COMPOUNDS;

EID: 79955589686     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200599d     Document Type: Article

References (34)

1. For reviews on umpolung of amine reactivity, see: Seebach, D.; Enders, D. Angew. Chem., Int. Ed. 1975, 14, 15
2. Beak, P.; Reitz, D. B. Chem. Rev. 1978, 78, 275
3. For selected examples of tin-lithium exchange of α-amino stannane followed by its functionalizations, see: Pearson, W. H.; Lindbeck, A. C. J. Org. Chem. 1989, 54, 5651
4. Pearson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc. 1991, 113, 8546
5. Chong, J. M.; Park, S. B. J. Org. Chem. 1992, 57, 2220
6. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715
7. Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574
8. Iula, D. M.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196
9. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625
10. Fraser, D. S.; Park, S. B.; Chong, J. M. Can. J. Chem. 2004, 82, 87
11. Coeffard, V.; Beaudet, I.; Evain, M.; Grognec, E. L.; Quintard, J.-P. Eur. J. Org. Chem. 2008, 3344
12. Stead, D.; Carbone, G.; O'Brien, P.; Campos, K. R.; Coldham, I.; Sanderson, A. J. Am. Chem. Soc. 2010, 132, 7260
13. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636 For a review on Stille coupling, see: Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704 and references cited therein
14. Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1990, 31, 2637
15. Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1
16. Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973
17. Kells, K. W.; Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666
18. Jensen, M. S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K. M.; Chung, J. Y. L.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 2, 1081
19. Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556
20. 3.
21. Kells, K. W.; Chong, J. M. Org. Lett. 2003, 5, 4215
22. He, A.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 6586
23. MacLeod, D.; Quayle, P.; Davies, G. M. Tetrahedron Lett. 1990, 31, 4927
24. Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622
25. For its application to organic synthesis, see: Mori, M.; Kaneta, N.; Isono, N.; Shibasaki, M. Tertahedron Lett. 1991, 43, 6139
26. Mori, M.; Isono, N.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1993, 58, 2972
27. Honda, T.; Mori, M. Chem. Lett. 1994, 1013
28. Kinoshita, A.; Mori, M. Chem. Lett. 1994, 1475
29. Imai, A. E.; Sato, Y.; Nishida, M.; Mori, M. J. Am. Chem. Soc. 1999, 121, 1217
30. Engberts, J. B. F. N.; Strating, J. Recl. Trav. Chim. Pays-Bas 1965, 84, 942
31. Kanazawa, A. M.; Denis, J.-N.; Greene, A. E. J. Org. Chem. 1994, 59, 1238
32. Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970
33. 3 reacted with an aldehyde in the presence of CsF-CsOH. See: Busch-Petersen, J.; Bo, Y.; Corey, E. J. Tetrahedron Lett. 1999, 40, 2065
34. 3/silica gel was employed as a stationary phase on column chromatography to remove organotin residues. See: Harrowven, D. C.; Curran, D. P.; Kostiuk, S. L.; Wallis-Guy, I. L.; Whiting, S.; Stenning, K. J.; Tang, B.; Packard, E.; Nanson, L. Chem. Commun. 2010, 46, 6335