Direct use of allylic alcohols in the allylation of sulfonylimidates

Chemical Communications

Volumn 46, Issue 45, 2010, Pages 8662-8664

  Matsubara, Ryosuke ^a   Masuda, Koichiro ^a   Nakano, Jyunya ^a   Kobayashi, Sh ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CINNAMYL ALCOHOL; DIOXANE; ELECTROPHILE; ESTER DERIVATIVE; SULFONYLIMIDATE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; HYDROLYSIS; STOICHIOMETRY; SUBSTITUTION REACTION;

EID: 78149434577     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc03067h     Document Type: Article

References (33)

1. S. Kobayashi R. Matsubara Chem.-Eur. J. 2009 15 10694
2. Trichloromethyl ketones: H. Morimoto S. H. Wiedemann A. Yamaguchi S. Harada Z. Chen S. Matsunaga M. Shibasaki Angew. Chem., Int. Ed. 2006 45 3146
3. N-acylanilides: S. Saito S. Kobayashi J. Am. Chem. Soc. 2006 128 8704
4. Acetonitrile: N. Kumagai S. Matsunaga M. Shibasaki J. Am. Chem. Soc. 2004 126 13632
5. sulfonylimidates: R. Matsubara F. Berthiol S. Kobayashi J. Am. Chem. Soc. 2008 130 1804
6. Thioamide: M. Iwata R. Yazaki Y. Suzuki N. Kumagai M. Shibasaki J. Am. Chem. Soc. 2009 131 18244
7. Palladium-catalyzed allylation of α-alkyl amides using a stoichiometric amount of strong base was reported; see: K. Zhang Q. Peng X.-L. Hou Y.-D. Wu Angew. Chem., Int. Ed. 2008 47 1741
8. S. B. J. Kan R. Matsubara F. Berthiol S. Kobayashi Chem. Commun. 2008 6354
9. J. Tsuji I. Shimizu I. Minami Y. Ohashi Tetrahedron Lett. 1982 23 4809
10. J. Tsuji I. Shimizu I. Minami Y. Ohashi T. Sugiura K. Takahashi J. Org. Chem. 1985 50 1523
11. M. Sakakibara A. Ogawa Tetrahedron Lett. 1994 35 8013
12. A. B. Zaitsev S. Gruber P. A. Plüss P. S. Pregosin L. F. Veiros M. Wörle J. Am. Chem. Soc. 2008 130 11604
13. I. Usui S. Schmidt M. Keller B. Breit Org. Lett. 2008 10 1207
14. A. B. Zaitsev S. Gruber P. S. Pregosin Chem. Commun. 2007 4692
15. I. F. Nieves D. Schott S. Gruber P. S. Pregosin Helv. Chim. Acta 2007 90 271
16. B. Trost J. Quancard J. Am. Chem. Soc. 2006 128 6314
17. M. Kimura M. Futamata R. Mukai Y. Tamaru J. Am. Chem. Soc. 2005 127 4592
18. C. García-Yebra J. P. Janssen F. Rominger G. Helmchen Organometallics 2004 23 5459
19. N. T. Patil Y. Yamamoto Tetrahedron Lett. 2004 45 3101
20. K. Manabe S. Kobayashi Org. Lett. 2003 5 3241
21. F. Ozawa H. Okamoto S. Kawagishi S. Yamamoto T. Minami M. Yoshifuji J. Am. Chem. Soc. 2002 124 10968
22. R. Takeuchi M. Kashio J. Am. Chem. Soc. 1998 120 8647
23. H. Bricout J.-F. Carpentier A. Mortreux J. Mol. Catal. A: Chem. 1998 136 243
24. I. Shimizu M. Toyoda T. Terashima M. Oshima H. Hasegawa Synlett 1992 301
25. D. E. Bergbreiter D. A. Weatherford J. Chem. Soc., Chem. Commun. 1989 883
26. X. Lu L. Lu J. Sun J. Mol. Catal. A: Chem. 1987 41 245
27. J.-P. Haudegond Y. Chauvin D. Commereuc J. Org. Chem. 1979 44 3063
28. K. E. Atkins W. E. Walker R. M. Manyik Tetrahedron Lett. 1970 11 3821
29. 3 is ongoing in our laboratory
30. The kinetic acidity of various sulfonylimidates has been studied quantitatively: R. Matsubara F. Berthiol H. V. Nguyen S. Kobayashi Bull. Chem. Soc. Jpn. 2009 82 1083
31. B. M. Trost D. L. Van Vranken Chem. Rev. 1996 96 395
32. Whether the arsinite ion 6 forms a covalent bond with π-allyl-Pd 7 is not clear.
33. For the other types of conversion of sulfonylimidates, see ref. 2d.