Zinc metal-promoted stereoselective olefination of aldehydes and ketones with gem-dichloro compounds in the presence of chlorotrimethylsilane
A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (1a) and methyl dichloroacetate (1b), to the corresponding cross- coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.
NEW SIMPLE METHOD FOR THE SYNTHESIS OF CIS-STILBENES
A new method involving catalytic acetylenic condensation as the key stage was developed for the synthesis of cis-stilbenes.Subsequent selective hydrogenation of the synthesized alkyltolanes over Pd-CaCO3 gave a series of alkyl-substituted stilbenes. 1,8-Dimethylphenanthrene was obtained from o-iodotoluene.
Merkushev, E. B.,Skorokhodova, T. S.
p. 308 - 311
(2007/10/02)
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