Michael Additions of Functionalized Organozinc Reagents Mediated by Catalytic Quantities of Copper (I)

Journal of the American Chemical Society

Volumn 117, Issue 22, 1995, Pages 6126-6127

  Lipshutz, Bruce H ^a   Wood, Michael R ^a   Tirado, Raymond ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000591250     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00127a028     Document Type: Article

References (13)

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3. Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919. See also: Hojo, M.; Harada, H.; Hosomi, A. Chem. Lett. 1994, 437.
4. Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. Nakamura, E.; Kuwajima, I. Org. Synth. 1988, 66, 43. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Nakamura, E. Synlett 1991, 539. Tamaru, Y.; Tanigawa, H.; Yamamoto, T.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1989, 28, 351.
5. Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5425.
6. Lipshutz, B. H. In Organometallics in Synthesis. A Manual; Schlosser, M., Ed., Wiley: New York, 1994; pp 283–382. Lipshutz, B. H.; Sengupta, S. Org. React. (New York), 1992, 41, 135.
7. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015; 6019. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047. Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029.
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9. 2, together with FG-RZnMe, did lead to the 1, 4-adduct in 67% yield upon warming to room temperature. Repeating this experiment, but adding additional MeLi (20 mol %) prior to quenching, increased the yield to 78%, further demonstrating the importance of added methyl ligands to the exchange process. For a related report based on a HO magnesio cuprate used stoichiometrically, see: Tucker, C. E.; Knochel, P. J. Org. Chem. 1993, 58, 4781.
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