Palladium(II)-Catalyzed Intramolecular Aminocarbonylation of endo-Carbamates under Wacker-Type Conditions

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2113-2122

  Harayama, Hiroto ^a   Abe, Atsuhiro ^a   Sakado, Tomonori ^a   Kimura, Masanari ^a   Fugami, Keigo ^a,b   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b GUNMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000454653     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961988b     Document Type: Article

References (27)

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3. Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. J. Am. Chem. Soc. 1988, 110, 3994-4002. See also, Bäckvall, J.-E.; Andersson, P. G. J. Am. Chem. Soc. 1990, 112, 3683-3685.
4. Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5731-5741.
5. Allenyl endo-carbamates (e.g., 2,3-butadienyl tosylcarbamate) smoothly undergo palladium(II)-catalyzed aminocarbonylation under the conditions similar to conditions A (in the presence of 3 equiv of sodium monochloroacetate): Kimura, M.; Saeki, N.; Uchida, S.; Harayama, H.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1993, 34, 7611-7614. For the related reaction of 4,5-hexadienylamines, see: Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009-6012.
6. Allenyl endo-carbamates (e.g., 2,3-butadienyl tosylcarbamate) smoothly undergo palladium(II)-catalyzed aminocarbonylation under the conditions similar to conditions A (in the presence of 3 equiv of sodium monochloroacetate): Kimura, M.; Saeki, N.; Uchida, S.; Harayama, H.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1993, 34, 7611-7614. For the related reaction of 4,5-hexadienylamines, see: Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009-6012.
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12. The use of MOA (and PO) was prompted by our previous experiences; the use of these additives greatly facilitated the Wacker-type dicarbonylation of homoallyl alcohols to provide α-[(methoxycarbonyl)methyl]-γ-butyrolactones: Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1009-1105.
13. For a similar stereoelectronic effect on cyclization reactions, see: McCombie, S. M.; Shankar, B. B.; Ganguly, A. K. Tetrahedron Lett. 1985, 26, 6301-6304.
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25. For the related discussion, see: Nilsson, Y. I. M.; Aranyos, A.; Andersson, P. G.; Bäckvall, J.-E.; Parrain, J.-L.; Plateau, C.; Quintard, J.-P. J. Org. Chem. 1996, 61, 1825-1829.
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