Pregled bibliografske jedinice broj: 780753
Sulfur Dioxide: a Powerful Tool for the Construction of Carbon-Carbon Bonds
Sulfur Dioxide: a Powerful Tool for the Construction of Carbon-Carbon Bonds // Stereoselective Synthesis of Drugs & Natural Products / Andrushko V., Andrushko N. (ur.).
New York (NY): John Wiley & Sons, 2013. str. 623-666
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Naslov
Sulfur Dioxide: a Powerful Tool for the Construction of Carbon-Carbon Bonds
Autori
Vogel, P. ; Markovic, D. ; Turks, M.
Vrsta, podvrsta i kategorija rada
Poglavlja u knjigama, ostalo
Knjiga
Stereoselective Synthesis of Drugs & Natural Products
Urednik/ci
Andrushko V., Andrushko N.
Izdavač
John Wiley & Sons
Grad
New York (NY)
Godina
2013
Raspon stranica
623-666
ISBN
9781118596784
Ključne riječi
Assymetric synthesis, sulfur dioxide, sulfur
Sažetak
For a long time, the use of sulfur dioxide in organic chemistry was limited to the synthesis of simple bulk materials such as sulfinate salts and sulfones. Conjugate bases of sulfones are carbon nucleophiles that can be used to construct C[BOND]C single bonds and stereoselective C[DOUBLE BOND]C double bonds. Sulfones can also be employed as electrophiles, for instance, in the stereo- and enantioselective α-aminoalkylations of carbonyl compounds. α, β-Unsaturated sulfones are excellent acceptors in asymmetric Michael additions. They are also good dienophiles. Sulfones and readily available sulfonyl chlorides are good electrophilic partners in desulfinylative C[BOND]C cross-coupling reactions catalyzed by transition metals, including iron. Sulfur dioxide undergoes reversible cheletropic additions with 1, 3-dienes and irreversible metallo-ene reactions with allylmetals. Conditions have been found realizing the endergonic H-ene reactions of SO2 with alkenes. This permits the one-pot synthesis of polyfunctional sulfinates, sulfones, and sulfonamides starting from alkenes. At a low temperature, the hetero-Diels-Alder additions of SO2 generate unstable sultines that can be used as electrophiles in the stereoselective construction of C[BOND]C bonds between electron-rich alkenes and 1, 3-dienes. The reaction cascade permits the one-pot construction of stereotriads and stereotetrads that can be used subsequently in two successive aldol reactions that give, in short ways (double chain elongation), long-chain polyketide and polypropionate antibiotics.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
