65144-04-9Relevant academic research and scientific papers
Metal chloride-promoted aldol reaction of α-dimethylsilylesters with aldehydes, ketones, and α-enones
Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
, p. 1917 - 1921 (2007/10/03)
In the presence of a catalytic amount of LiCl, α-dimethylsilylesters (α-DMS-esters) 1 smoothly reacted with various aldehydes at 30°C to give aldols in good to high yields. On the other hand, the aldol reaction with ketones was effectively promoted by MgCl2 rather than by LiCl. α-Enones also underwent the metal chloride-promoted addition of 1 at the carbonyl carbon or β-carbon. Georg Thieme Verlag Stuttgart.
Reactivity of α-Metal(group 4) Esters. Lewis Acid Mediated Reactions of α-Triphenyltin Esters with Aldehydes and Acetals
Kiyooka, Syun-ichi,Nakata, Masumi
, p. 721 - 722 (2007/10/02)
Ethyl triphenylstannylacetate and ethyl α-triphenylstannylpropionate reacted with aldehydes and acetals to give β-hydroxy and β-alkoxy esters at room temperature in the presence of TiCl4 in moderate yields.Under these conditions ethyl triphenylgermylacetate and ethyl trimethylsilylacetate did not work.
DIASTEREOFACIAL SELECTIVITY VIA ALDOL REACTIONS USING ETHYL DITHIOACETATE AND ETHYL DITHIOPROPIONATE ENOLATES
Meyers, A. I.,Walkup, Robert D.
, p. 5089 - 5106 (2007/10/02)
The lithium enolate of ethyl dithioacetate reacts with α-methyl aldehydes to yield the aldol products in which the syn configuration in the positions β and γ to the thiocarbonyl of the product is favored over the anti configuration.This selectivity is solvent-dependent, and is enhanced at lower temperatures.In most cases, syn:anti product ratios obtained under these conditions varied from 57:43 to >99:1, depending upon the structure of the α-methyl aldehyde.When the lithium enolate of ethyl dithiopropionate was allowed to react with α-methyl aldehydes, only two out of the four possible diastereomers were detected in the product mixtures.
ALDOL CONDENSATIONS OF ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE AND ETHYL 1,3-DITHIANE-2-CARBOXYLATE WITH CHIRAL ALDEHYDES. EXCEPTIONAL DIASTEREOFACE SELECTIVITY FROM TWO CONVENIENT ACETATE EQUIVALENTS.
Flippin, Lee A.,Dombroski, Mark A.
, p. 2977 - 2980 (2007/10/02)
Lithium enolates derived from the title esters show high diastereoface selectivity in their reactions with chiral aldehydes.The resulting 2,2-dithioaldols are desulfurized in good yield with Ni2B-H2 (EtOH, 20 deg C).With this mild desulfurization protocol, complete retention of stereochemical integrity was observed for all isolated aldols.
