Regio- and stereoselective hydroamidation of 1-alkynylphosphine sulfides catalyzed by cesium base

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3093-3095

  Kondoh, Azusa ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 58149331596     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8010979     Document Type: Article

References (25)

1. (a) Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4099-4104.
2. (b) Kondoh, A.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 1383-1385.
3. (c) Kanemura, S.; Kondoh, A.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 2031-2033.
4. (d) Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 6996-6997.
5. (a) Rönnholm, P.; Södergren, M.; Hilmersson, G. Org. Lett. 2007, 9, 3781-3783.
6. (b) Krauss, I. J.; Leighton, J. L Org. Lett. 2003, 5, 3201-3203, and references cited therein.
7. (c) Anderson, C.; Cubbon, R. J.; Harling, J. D. Tetrahedron: Asymmetry 2001, 12, 923-935.
8. (d) Ito, M.; Ikariya, T. Chem. Commun. 2007, 5134-5142.
9. For recent reviews of catalytic hydroaminations and hydroamidations. (a) Severin, R.; Doye, S. Chem. Soc. Rev. 2007, 36, 1407-1420.
10. (b) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
11. (c) Hong, S.; Marks, T. Acc. Chem. Res. 2004, 37, 673-686.
12. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
13. (e) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 4.
14. For recent examples of intermolecular hydroamidation of alkynes, see: (a) Yudha, S. S.; Kuninobu, Y.; Takai, K. Org. Lett. 2007, 9, 5609-5611.
15. (b) Goossen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem., Int. Ed. 2005, 44, 4042-4045.
16. (c) Kondo, T.; Tanaka, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414.
17. For base-mediated additions of tosylamides to propiolates, see: (a) Barbazanges, M.; Meyer, C.; Cossy, J. Org. Lett. 2007, 9, 3245-3248.
18. (b) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S.; Chung, C. K. Tetrahedron Lett. 1995, 36, 417-420.
19. The X-ray crystallographic analysis of 3ca verified the E stereochemistry of the major isomers. See the Supporting Information.
20. For recent reviews, see: (a) Källström, K.; Munslow, I.; Andersson, P. G. Chem. -Eur. J. 2006, 12, 3194-3200.
21. (b) Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272-3296.
22. (a) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tajani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
23. (b) Togni, A. Angew. Chem., Int. Ed. 1996, 35, 1475-1477.
24. When (R)-BINAP was used as a ligand instead of 7, 91% ee of 6a was obtained in 82% yield. However, (R)-BINAP was less effective for the enantioselective hydrogenation of 3af to provide 6b in 99% yield with 15% ee.
25. Romeo, R.; Wozniak, L. A.; Chatgilialoglu, C. Tetrahedron Lett. 2000, 41, 9899-9902.