Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones

Organic Letters

Volumn 15, Issue 14, 2013, Pages 3750-3753

  Jinzaki, Takaaki ^a   Arakawa, Mitsuru ^b   Kinoshita, Hidenori ^a   Ichikawa, Junji ^b   Miura, Katsukiyo ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84880546569     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401663u     Document Type: Article

References (27)

1. Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 31, 1
2. Kaiser, E. W.; Hauser, C. R. J. Org. Chem. 1968, 33, 3402
3. Zhou, J. J. P.; Zhoug, B.; Silverman, R. B. J. Org. Chem. 1995, 60, 2261
4. Li, N.-S.; Yu, S.; Kabalka, G. W. J. Org. Chem. 1995, 60, 5973
5. Araki, S.; Yamada, M.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1994, 67, 1126
6. Takai, K.; Ueda, T.; Ikeda, N.; Morikawa, T. J. Org. Chem. 1996, 61, 7990
7. Bianchi, G.; Feroci, M.; Rossi, L. Eur. J. Org. Chem. 2009, 3863
8. Barhdadi, R.; Gal, J.; Heintz, M.; Troupel, M.; Péichon, J. Tetrahedron 1993, 49, 5091
9. Goto, A.; Endo, K.; Ukai, J.; Irle, S.; Saito, S. Chem. Commun 2008, 2212
10. Kumagai, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 13632
11. Suto, Y.; Kumagai, N.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 3147
12. Kisanga, P.; McLeod, D.; D'Sa, B.; Verkade, J. J. Org. Chem. 1999, 64, 3090
13. Latouche, R.; Texier-Boullet, F.; Hameli, J. Tetrahedron Lett. 1991, 32, 1179
14. Palomo, C.; Aizpurua, J. M.; Lopez, M. C.; Lecea, B. J. Chem. Soc., Perkin Trans. 1 1989, 1692
15. Mukaiyama and co-workers have reported carbonyl addition of TMS-acetonitrile under catalysis by AcOLi. In addition, they have found that α-alkylated TMS-acetonitriles add efficiently to benzaldehyde under catalysis by AcOCs (three examples). Kawano, Y.; Kaneko, N.; Mukaiyama, T. Chem. Lett. 2005, 34, 1508
16. Wadhwa, K.; Verkade, J. G. J. Org. Chem. 2009, 74, 5683
17. Matsukawa, S.; Kitazaki, E. Tetrahedron Lett. 2008, 49, 2982
18. Jolivet, S.; Abdallah-El Ayoubi, S.; Mathe, D.; Texier-Boullet, F.; Hamelin, J. J. Chem. Res. Synop. 1996, 6, 300
19. For enantioselective carbonyl addition of silyl ketene imines, see: Denmark, S. E.; Wilson, T. W.; Burk, M. T.; Heemsta, J. R., Jr. J. Am. Chem. Soc. 2007, 129, 14864
20. Miura, K.; Ebine, M.; Ootsuka, K.; Ichikawa, J.; Hosomi, A. Chem. Lett. 2009, 38, 832
21. Miura, K.; Nakagawa, T.; Hosomi, A. Synlett 2003, 2068
22. Miura, K.; Nakagawa, T.; Hosomi, A. J. Am. Chem. Soc. 2002, 124, 536
23. Miura, K.; Nakagawa, T.; Hosomi, A. Synlett 2005, 1917
24. A similar Zn-mediated method is valuable for the synthesis of TMS-acetonitrile. For the original method, see: Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc., Perkin Trans. 1 1979, 26
25. Iwanami, K.; Oriyama, T. Synlett 2006, 112
26. Génisson, Y.; Gorrichon, L. Tetrahedron Lett. 2000, 41, 4881
27. Naked enolates generated from ester silyl enolates and α-silyl esters deprotonate enolizable ketones efficiently. Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181