36471-61-1Relevant articles and documents
The zirconium alkoxide-catalyzed aldol-tishchenko reaction of ketone aldols
Schneider, Christoph,Hansch, Markus,Weide, Timo
, p. 3010 - 3021 (2007/10/03)
The aldol-Tishchenko reaction of ketone aldols as enol equivalents has been developed as an efficient strategy to furnish differentiated 1,3-anti-diol monoesters in one step. The thermodynamically unstable ketone aldols undergo a facile retro-aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol-Tishchenko reaction in typically high yields and with complete 1,3-anti diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3-anti-diol monoesters, which may be hydrolyzed to the corresponding 1,3-anti-diols.
In search of open-chain 1,3-stereocontrol
Barbero, Asun,Blakemore, David C.,Fleming, Ian,Wesley, Robert N.
, p. 1329 - 1352 (2007/10/03)
Methylation of methyl 4-phenylpentanoate 25 gives the diastereoisomers methyl (2RS,4SR)-2-methyl-4-phenylpentanoate 26 and methyl (2RS,4RS)- 2-methyl-4-phenylpentanoate 27 in a ratio of 44:56. The aldehydes 3-dimethyl(phenyl)silylbutanal 28, 3-dimethyl(ph
Asymmetric Synthesis of (3R,5R)- and (3S,5S)-2,6-Dimethylheptane-3,5-diol, useful C2 Chiral Auxiliaries
Jacoby, C.,Braekman, J.C.,Daloze, D.
, p. 753 - 756 (2007/10/02)
(R,R)- and (S,S)-2,6-Dimethylheptane-3,5-diol, which are useful C2 chiral auxiliaries, have been both synthesized in high optical purity from 2,6-dimethylheptane-3,5-dione, by using as key step a Sharpless kinetic resolution.
