A Remarkable Steric Effect in Palladium-Catalyzed Grignard Coupling: Regio- and Stereoselective Monoalkylation and -arylation of 1,1-Dichloro-l-alkenes

Journal of the American Chemical Society

Volumn 109, Issue 4, 1987, Pages 1257-1258

  Minato, Akio ^a   Suzuki, Keizo ^a   Tamao, Kohei ^b  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845283423     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00238a052     Document Type: Article

References (9)

1. Minato, A.; Kawano, S.; Suzuki, K.; Tamao, K.; Kumada, M., presented in the Fifth International Conference on Organic Synthesis, Freiburg, FRG, Aug. 27–30, 1984; abstract, p 44.
2. Recent papers: (a) Negishi, E. I. ; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821. (b) Negishi, E. I. In Current Trends in Organic Synthesis; Nozaki, H., Ed.; Pergamon: Oxford, 1983; pp 269–280. (c) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (d) Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831. (e) Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943. (f) Sheffy, F. K.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 7175. (g) Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 452. (h) Sharp, M. J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997. (i) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1985, 932, (j) Nwokogu, G. C. J. Org. Chem. 1985, 50, 3900. (k) Satoh, M.; Miyaura, N.; Suzuki, A. Chem. Lett, 1986, 1329.
3. Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Suzuki, K.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511.
4. Mp 51-52 °C (EtOH); lit. mp 52-54 °C: Cristol, S. J.; Bly, R. S., Jr. J. Am. Chem. Soc. 1961, 83, 4027.
5. Helquist, P. Tetrahedron Lett. 1978, 22, 1913.
6. Fitton, P.; McKeon, J. E. J. Chem. Soc., Chem. Commun. 1968, 4. Johnson, F. G.; Lewis, J.; Jones, J. D.; Taylor, K.A. J. Chem. Soc., Dalton Trans. 1974, 34. Carvajal, J.; Muller, G.; Sales, J.; Solans, X.; Miravitlles, C. Organometallics 1984,3, 966. Moritani, L; Fujiwara, Y.; Danno, S. J. Organomet. Chem. 1971, 27, 279. Ratovelomanana, U.; Linstrumelle, G.; Normant, J. F. Tetrahedron Lett. 1985, 26, 2575.
7. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
8. Rabinowitz, R.; Marcus, R. J. Am. Chem. Soc. 1962, 84, 1312. Villieras, J.; Perriot, P.; Normant, J. F. Synthesis, 1975, 458. Hosomi, A.; Inaba, M.; Sakurai, H. Tetrahedron Lett. 1983, 24, 4727 and references cited therein.
9. Cadogan, J.I.G. Organophosphorous Reagents in Organic Synthesis; Academic: London, 1979.