770-62-7Relevant articles and documents
Novel synthetic approach to the 8,10-dimethyl anti-syn-anti-perhydrophenanthrene skeleton
Coltart, Don M.,Danishefsky, Samuel J.
, p. 1289 - 1292 (2007/10/03)
(Matrix presented) An efficient and highly stereocontrolled approach to the 8,10-dimethyl anti-syn-anti-perhydrophenanthrene carbon skeleton starting with the Wieland-Miescher ketone is described. The approach centers on a Diels-Alder-angular methylation-
α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION
Paterson, Ian
, p. 4207 - 4220 (2007/10/02)
For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.
STEREOCHIMIE - LIV. INFLUENCE DU DEGRE DE SUBSTITUTION DE LA DOUBLE LIAISON ETHYLENIQUE SUR LA STEREOCHIMIE DE L'HYDROCYANATION 1,4 DE CETONES CONJUGUEES
Agami, C.,Fadlallah, M.,Levisalles, J.
, p. 909 - 914 (2007/10/02)
The topological isomerism between octalinones in which the enone group has two distinct locations does not lead to any difference on the stereochemistry of the hydrocyanation of these substrates; the cyano group is axial in the kinetically controlled products.On the contrary, the stereoselectivity is strikingly reversed when the enone group is substituted by a methyl β to the carbonyl, leading to the introduction of the cyano group in an equatorial configuration in the kinetically controlled products.
