Stereospecific Alkylation of Cyclopropyl Bromides by Means of Dibutylcopperlithium and Alkyl Halides

Journal of the American Chemical Society

Volumn 99, Issue 17, 1977, Pages 5816-5817

  Yamamoto, Hajime ^a   Kitatani, Katuzi ^a   Hiyama, Tamejiro ^a   Nozaki, Hitosi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847089969     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00459a056     Document Type: Article

References (19)

1. R. Noyori, “Transition Metal Organometallics in Organic Synthesis”, Vol. 1, H. Alper, Ed., Academic Press, New York, N.Y., 1976 p 83.
2. G. H. Posner, Org. React, 22, 253(1975); (b)J. F. Normant, Synthesis, 63 (1972). (c) Reduction by means of copper hydride: S. Masamune, G. S. Bates, and P. E. Georghiou, J. Am. Chem. Soc., 96, 3686 (1974), and references cited therein.
3. K. Kitatani, T. Hiyama, and H. Nozaki, J. Am. Chem. Soc., 98, 2362 (1976); Bull. Chem. Soc. Jpn., 50, 1600 (1977).
4. This type of reaction is taken for a side reaction in ref 2a and in E. J. Corey and G. H. Posner, J. Am. Chem. Soc., 90, 5615 (1968)
5. A remarkably successful instance is seen in E. J. Corey and I. Kuwajima, J. Am. Chem. Soc., 92, 395 (1970) (see also J. P. Marino and D. M. Floyd, J. Am. Chem. Soc., 96, 7138 (1974);
6. G. M. Whitesides, W. F. Fischer, Jr., J. S. Flippo, Jr., R. W. Bashe, and H. O. House,J. Am. Chem. Soc., 91, 4871 (1969)).
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11. T. Ando, K. Wakabayashi, H. Yamanaka, and W. Funasaka, Bull. Chem. Soc. Jpn., 45, 1576 (1972);
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14. T. Shirafuji, K. Oshima, Y. Yamamoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 44, 3161 (1971);
15. P. Warner and S.-L. Lu, Tetrahedron Lett., 4665 (1976);
16. K. Kitatani, T. Hiyama, and H. Nozaki, Bull. Chem. Soc. Jpn., in press.
17. S. R. Wilson and K. A. Prodan, Tetrahedron Lett., 4231 (1976). We are indebted to Professor Wilson for sending us authentic samples of methyl cascarillate and its cis isomer.
18. K. Kitatani, T. Hiyama, and H. Nozaki, J. Am. Chem. Soc., 97, 949 (1975); Bull. Chem. Soc. Jpn., in press.
19. E. J. Corey and P. Ulrich, Tetrahedron Lett., 3685 (1975).