Journal
GREEN CHEMISTRY
Volume 13, Issue 5, Pages 1280-1287Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1gc15064b
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Funding
- Ministry of Science and Higher Education [N N204 178340]
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A novel organocatalytic procedure for the direct aldol reaction of unprotected acetol and activated aromatic aldehydes catalyzed by 9-amino-9-epi-Cinchona ditartrates is presented. The protocol presented avoids the use of problematic solvents and toxic reagents as well as chromatographic purification of the products - instead a simple extraction has been applied for the isolation of pure aldols from the reaction mixture. This catalytic system provides exclusively linear aldols with quantitative yields and good syn-diastereoselectivity and enantioselectvitiy up to 90% ee. Further upgrading of the enantiomeric excess of syn-aldols up to 99% ee is easily accomplished by a single and reliable crystallization. The use of cinchonine or quinine-derived catalysts gives access to both enantiomers of syn-aldols for which the absolute configuration has been determined by X-ray diffraction. The operationally convenient and scalable organocatalytic procedure using cheap and renewable chemicals - both acetol and the catalysts, offers a sustainable and green way for the synthesis of a number of alpha-keto-syn-diols.
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