Conclusions
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1.
The directed aldol condensation with higher aldehydes and aldimines, including functionally substituted compounds, can serve as a highly stereoselective preparative method for the production of the E-disubstituted acroleins, which are readily transformed into the corresponding Z-trisubstituted olefins.
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2.
The potentialities of the method are illustrated by the synthesis of the heptaprenols ωtttcccOH and ωtttcctOH.
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Literature cited
N. Ya. Grigor'eva and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 2644.
N. Ya. Grigor'eva (Grigorieva), I. M. Avrutov, and A. V. Semenovskii (Semenovsky), Tetrahedron Lett.,24, 5531 (1983).
A. M. Moiseenkov, M. A. Novikova, E. V. Polunin, and S. I. Torgova, Izv. Akad. Nauk SSSR, Ser. Khim.,1983, 1557.
W. C. Still and C. Gennar, Tetrahedron Lett.,24, 4405 (1983).
K. Sato, O. Miyamoto, S. Inoue, F. Furusawa, and Y. Matsuhashi, Chem. Lett.,1983, 725.
V. N. Shibaev, Usp. Biol. Khim.,17, 187 (1976).
G. Witting and H. D. Frommeld, Chem. Ber.,97, 3548 (1964).
E. O. Wilson, W. H. Bossert, and F. E. Regnier, J. Insect Physiol.,15, 597 (1969).
E. J. Corey and H. Yamamoto, J. Am. Chem. Soc.,92, 226 (1970).
E. P. Prokof'ev, N. Ya. Grigor'eva, and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1980, 834.
N. Ya. Grigor'eva, E. P. Prokof'ev, and A. V. Semenovskii, Dokl. Akad. Nauk SSSR,245, 366 (1979).
K. Ya. Burshtein and N. Ya. Grigor'eva, Izv. Akad. Nauk SSSR, Ser. Khim.,1982, 449.
E. J. Corey and K. J. Achiwa, J. Org. Chem.,34, 3667 (1969).
A. S. Shashkov, N. Ya. Grigor'eva, I. M. Avrutov, A. V. Semenovskii, V. N. Odinokov, V. K. Ignatyuk, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim.,1979, 388.
E. J. Corey, D. Enders, and M. G. Bock, Tetrahedron Lett.,1976, 7.
A. V. Semenovskii, N. Ya. Grigor'eva, I. M. Avrutov, V. V. Veselovskii, M. A. Novikova, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim.,1984, 152.
N. Ya. Grigor'eva, I. M. Avrutov, A. V. Semenovskii, V. N. Odinokov, V. R. Akhunova, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim.,1979, 382.
E. E. van Tamelen and T. J. Curphey, Tetrahedron Lett.,1962, 121.
J. F. Bielmann and J. D. Ducep, Tetrahedron,27, 5861 (1971).
G. Büchi and H. Wüest, J. Org. Chem.,34, 1122 (1969).
E. J. Corey, H. Yamamoto, D. K. Herron, and K. J. Achiwa, J. Am. Chem. Soc.,92, 6635 (1970).
J. H. Babler and M. J. Coghlan, Tetrahedron Lett.,1979, 1971.
S. M. Makin, R. N. Kruglikova, T. P. Popova, and A. I. Chernyshev, Zh. Org. Khim.,18, 960 (1982).
K. Sato and S. Morii, Ashahi Garasu Kogyo Gijutsu Shoreikai Kenkyu Hokoku,29, 199 (1976); Ghem. Abs.,89, 197734j (1978).
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For the previous communications, see [1, 2].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1824–1835, August, 1985.
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Grigor'eva, N.Y., Avrutov, I.M., Pinsker, O.A. et al. Directed aldol condensation as a stereoselective method for the synthesis of Z-trisubstituted olefins. Russ Chem Bull 34, 1673–1685 (1985). https://doi.org/10.1007/BF00948516
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DOI: https://doi.org/10.1007/BF00948516