Intramolecular, Stoichiometric (Li, Mg, Zn) and Catalytic (Ni, Pd, Pt) Metallo‐Ene Reactions in Organic Synthesis [New Synthetic Methods (75)]
Tóm tắt
Metallo‐ene reactions, hardly recognized until very recently, have experienced a breathtaking development when applied in an intramolecular sense. Efficient regio‐ and stereoselective magnesium‐ene cyclizations have served as a cornerstone for numerous syntheses of structurally diverse natural products (e.g., sesquiterpenes of marine or plant origin, alkaloids, fragrances, insect defense compounds, and a fungitoxin). A brilliant example is the synthesis of the elusive odorant (+)‐khusimone which outshines 20 years of work in the field of tricyclovetivane synthesis. Palladium‐, platinum‐, and nickel‐catalyzed versions of the metallo‐ene reaction are in a comparatively early stage of exploration, but, nevertheless, reveal intriguing potential. Hence an almost 100% stereospecific CO→C;Pd‐→ CC chirality transfer permits simple and selective,
Từ khóa
Tài liệu tham khảo
Lehmkuhl H., Bull. Soc. Chim. Fr. Part II, 1981, 87
Frangin Y., Bull. Soc. Chim. Fr., 1976, 1173
Bernadou F., Tetrahedron Lett., 1976, 3083
Mikhailov B. M., Tetrahedron Lett., 1971, 2127
Bubnov Yu. N., Tetrahedron Lett., 1971, 2153
Ciganek E., 1984, Org. React., 32, 1
Felkin H., Tetrahedron Lett., 1972, 2285
Felkin H., J. Chem. Soc. Chem. Commun., 1975, 242
(c)H.Fukutani M.Takizawa H.Okada Jpn. Pat.7239 034 (1972);
1973, Chem. Abstr., 78, 111 498
Courtois G., 1978, C. R. Séances Acad. Sci. Ser. C, 286, 265
W.Oppolzer T.Inokuchi unpublished results.
Oppolzer W., 1982, J. Am Chem. Soc., 104, 6578
Collman J. P., 1987, Principles and Applications of Organometallic Chemistry, 881
(a)W.Oppolzer J. M.Gaudin R. E.Swenson J.‐P.Barras presented (W. O.) at the 3eCongrès national de la Société Française de Chimie Nice September 5 1988;
(b)W.Oppolzer R. E.Swenson W.Pachinger Helv. Chim. Acta in press.
Oppolzer W., 1988, Chimia, 42, 6
W.Oppolzer D.Kuo unpublished results.
W.Oppolzer M.Bedoya‐Zurita C. Y.Switzer Tetrahedron Lett. in press.