Reacție Sakurai

Reacția Sakurai sau reacția Hosomi-Sakurai este o reacție organică ce are loc între carbon-electrofili (precum o cetonă) și aliltrimetilsilan, fiind catalizată de un acid Lewis tare.^[1]^[2]^[3]^[4]^[5]^[6]^[7] Reacția a fost denumită după chimiștii japonezi Akira Hosomi și Hideki Sakurai.

Note

^ Sakurai, Hideki; Hosomi, Akira; Kumada, Makoto (1969). „Addition of trichloromethyl radicals to alkenylsilanes”. The Journal of Organic Chemistry. 36 (4): 1764–1768. doi:10.1021/jo01258a052.
^ Hosomi, Akíra; Sakurai, Hideki (1 aprilie 1976). „Syntheses of γ,δ-unsaturated alcohols from allylsilanes and carbonyl compounds in the presence of titanium tetrachloride”. Tetrahedron Letters. 17 (16): 1295–1298. doi:10.1016/S0040-4039(00)78044-0. ISSN 0040-4039.
^ Hosomi, Akira; Endo, Masahiko; Sakurai, Hideki (5 septembrie 1976). „Allylsilanes as synthetic intermediates. ii. syntheses of homoallyl ethers from allylsilanes and acetals promoted by titanium tetrachloride”. Chemistry Letters. 5 (9): 941–942. doi:10.1246/cl.1976.941  . ISSN 0366-7022.
^ Hosomi, Akira; Sakurai, Hideki (1 martie 1977). „Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enones”. Journal of the American Chemical Society. 99 (5): 1673–1675. doi:10.1021/ja00447a080. ISSN 0002-7863.
^ Hosomi, Akira (1 mai 1988). „Characteristics in the reactions of allylsilanes and their applications to versatile synthetic equivalents”. Accounts of Chemical Research. 21 (5): 200–206. doi:10.1021/ar00149a004. ISSN 0001-4842.
^ Fleming, Ian; Dunoguès, Jacques; Smithers, Roger (2004), „The Electrophilic Substitution of Allylsilanes and Vinylsilanes”, Organic Reactions (în engleză), American Cancer Society, pp. 57–575, doi:10.1002/0471264180.or037.02, ISBN 9780471264187
^ Fleming, Ian (1 ianuarie 1991). „Allylsilanes, Allylstannanes and Related Systems”. În Trost, Barry M.; Fleming, Ian. 2.2 - Allylsilanes, Allylstannanes and Related Systems. Comprehensive Organic Synthesis. Pergamon. pp. 563–593. doi:10.1016/b978-0-08-052349-1.00041-x. ISBN 9780080523491. Accesat în 1 septembrie 2019.

Vezi și

Reacție Grignard

[1] Sakurai, Hideki; Hosomi, Akira; Kumada, Makoto (1969). „Addition of trichloromethyl radicals to alkenylsilanes”. The Journal of Organic Chemistry. 36 (4): 1764–1768. doi:10.1021/jo01258a052.

[2] Hosomi, Akíra; Sakurai, Hideki (1 aprilie 1976). „Syntheses of γ,δ-unsaturated alcohols from allylsilanes and carbonyl compounds in the presence of titanium tetrachloride”. Tetrahedron Letters. 17 (16): 1295–1298. doi:10.1016/S0040-4039(00)78044-0. ISSN 0040-4039.

[3] Hosomi, Akira; Endo, Masahiko; Sakurai, Hideki (5 septembrie 1976). „Allylsilanes as synthetic intermediates. ii. syntheses of homoallyl ethers from allylsilanes and acetals promoted by titanium tetrachloride”. Chemistry Letters. 5 (9): 941–942. doi:10.1246/cl.1976.941  . ISSN 0366-7022.

[4] Hosomi, Akira; Sakurai, Hideki (1 martie 1977). „Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enones”. Journal of the American Chemical Society. 99 (5): 1673–1675. doi:10.1021/ja00447a080. ISSN 0002-7863.

[5] Hosomi, Akira (1 mai 1988). „Characteristics in the reactions of allylsilanes and their applications to versatile synthetic equivalents”. Accounts of Chemical Research. 21 (5): 200–206. doi:10.1021/ar00149a004. ISSN 0001-4842.

[6] Fleming, Ian; Dunoguès, Jacques; Smithers, Roger (2004), „The Electrophilic Substitution of Allylsilanes and Vinylsilanes”, Organic Reactions (în engleză), American Cancer Society, pp. 57–575, doi:10.1002/0471264180.or037.02, ISBN 9780471264187

[7] Fleming, Ian (1 ianuarie 1991). „Allylsilanes, Allylstannanes and Related Systems”. În Trost, Barry M.; Fleming, Ian. 2.2 - Allylsilanes, Allylstannanes and Related Systems. Comprehensive Organic Synthesis. Pergamon. pp. 563–593. doi:10.1016/b978-0-08-052349-1.00041-x. ISBN 9780080523491. Accesat în 1 septembrie 2019.

[1]

[2]

[3]

[4]

[5]

[6]

[7]