Palladium(0)-catalyzed coupling of allenyl N-tosylcarbamates with hypervalent iodonium salts

Tetrahedron

Volumn 55, Issue 22, 1999, Pages 6863-6870

  Kang, Suk Ku ^a   Baik, Tae Gon ^a   Yun, Hur ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033612124     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00340-3     Document Type: Article

References (13)

1. Kimura M, Fugami K, Tanaka S, Tamaru Y. J. Org. Chem. 1992;57;6377-6379.
2. Kimura M, Fugami K, Tanaka S, Tamaru Y. Tetrahedron Lett. 1991;32:6359-6362.
3. The palladium-catalyzed cyclization of allenic amines and alcohols were reported by Gallagher et al. and Walkup et al. In these reports, they used exess iodobenzene (5 equiv). See, (a) Davies IW, Scopes DIC, Gallagher T. Synlett 1993;85-87
4. (b) Walkup RD, Guan L, Mosher MD, Kim SW, Kim Y S. Synlett 1993;88-90.
5. Kimura M, Saeki N, Uchida S, Harayama H, Tanaka S, Fugami K, Tamaru Y. Tetrahedron Lett. 1993;34:7611-7614.
6. Kang S-K, Baik TG, Kulak AN. Synlett 1999 in press.
7. Stang T-J, Zhdankin VV. Chem. Rev. 1996;16:1123-1178.
8. Friesen RW, Kolaczewska AE. J. Org. Chem. 1991;56:4888-4895.
9. For the preparation of 3-methyl-substitute allenol. See, Konegawa T, Ohtsuka Y, Ikeda H, Sugai T, Ohta H. Synlett 1997;1297-1299.
10. 1H NMR spectrum (300 MHz). Irradiation of C(5) proton (1.98 ppm) results in an NOE enhancement (5.7%) of the C(6) proton (5.34 ppm). The formation of cis-product is known. See, Trost BM, Sudhakar AR. J. Am. Chem. Soc. 1988;110:7933-7935. (Equation presented)
11. A different mechanism which involves the nucleophilic attack of the carbamate moiety to form vinylpalladium intermediate which is subsequently subjected to reductive elimination cannot be eliminated.
12. Recently Trost et al. reported the palladium-catalyzed carbocyclization of allenyl derivatives to form nine- and ten-membered rings. See, Trost BM, Michellys PY, Gerusz VJ. Angew. Chem. Int. Ed. Engl. 1997;1750-1753.
13. 3CN at reflux for 3 h by the procedure of Walkup and Gallagher gave a complex mixture of products, which were separated to afford the product 3h in a low (27%) yield.