An Organozinc Aid in Alkylation and Acylation of Lithium Enolates

Journal of Organic Chemistry

Volumn 54, Issue 8, 1989, Pages 1785-1787

  Morita, Yasushi ^a   Suzuki, Masaaki ^a   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845183574     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00269a006     Document Type: Letter

References (13)

1. Reviews: (a) House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin: Menlo Park, CA, 1972; Chapters 9–11. (b) Augustine, R. L. Carbon-Carbon Bond Formation; Marcel Dekker: New York, 1979; Vol. 1.
2. For some examples, see: (a) Tardella, P. A. Tetrahedron Lett. 1969, 1117. (b) House, H. O.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1971, 36, 2361. (c) Borowitz, I. J.; Casper, E. W. R.; Crouch, R. K.; Yee, K. C. 1972, 37, 3873. (d) Posner, G. H.; Sterling, J. J.; Whitten, C. E.; Lentz, C. M.; Brunelle, D. J. J. Am. Chem. Soc. 1975, 97, 107.
3. Review: Hauser, C. R.; Swamer, F. W.; Adams, J. T. Org. React. 1954, 8, 59.
4. Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737. (b) Posner, G. H.; Lentz, C. M. J. Am. Chem. Soc. 1979, 101, 934. (c) Johnson, C. R.; Penning, T. D. 1988,110, 4726 and references cited therein.
5. Beck, A. K.; Hoekstra, M. S.; Seebach, D. Tetrahedron Lett. 1977, 1187.
6. Howard, A. S.; Meerholz, C. A.; Michael, J. P. Tetrahedron Lett. 1979. 1339.
7. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425.
8. For structures of lithium enolates, see: Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
9. For chemistry of chlorozinc enolates, see: (a) House, H. O.; Crumrine, D. S.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310. (b) Heng, K. K.; Smith, R. A. J. Tetrahedron 1979, 35, 425. (c) Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45,1066. For alkylzinc enolates, see: (d) Kataoka, K.; Tsuruta, T. Polym. J. 1977, 9, 595. (e) Hansen, M. M.; Bartlett, P. A.; Heathcock, C. H. Organometallics 1987, 6, 2069.
10. Isobe, M.; Kondo, S.; Nagasawa, N.; Goto, T. Chem. Lett. 1977, 679. (b) Tiickmantel, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119,1581. (c) Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron Lett. 1988, 29, 3593. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988, 53, 4133 and references cited therein.
11. Noyori, R.; Suzuki, M. Angew. Chem., Int. Ed. Engl. 1984, 23, 847. (b) Suzuki, M.; Yanagisawa, A.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 3348. (c) Suzuki, M.; Yanagisawa, A.; Noyori, R. 1988, 110, 4718.
12. For a convenient way to 7, see: Kitano, Y.; Matsumoto, T.; Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F. Chem. Lett. 1987, 1523.
13. Suzuki, M.; Kawagishi, T.; Yanagisawa, A.; Suzuki, T.; Okamura, N.; Noyori, R. Bull. Chem. Soc. Jpn. 1988, 61, 1299. (b) Tanaka, T.; Hazato, A.; Bannai, K.; Okamura, N.; Sugiura, S.; Manabe, K.; Toru, T.; Kurozumi, S.; Suzuki, M.; Kawagishi, T.; Noyori, R. Tetrahedron 1987, 43, 813.