Abstract
A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.
Highlights
The enantioselective aldol reaction is among the most important synthetic tools for C–C bond formation in organic synthesis [1,2,3]
Diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities
Arylglyoxals are endogenous α-oxoaldehydes that have been extensively used as electrophiles in related enantioselective aldol processes to afford synthetically important chiral 2-hydroxy-1,4-dicarbonyl compounds [4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19]
Summary
The enantioselective aldol reaction is among the most important synthetic tools for C–C bond formation in organic synthesis [1,2,3]. In 2009, Feng and coworkers developed an asymmetric aldol-type reaction between arylglyoxal derivatives and. Hayashi and coworkers reported a chiral diarylprolinol-catalyzed direct aldol reaction of glyoxal derivatives with aldehydes, affording chiral 2-hydroxy-1,4-dicarbonyl compounds with good experimental outcomes [6]. Reported examples have mainly focused on the catalytic asymmetric synthesis of α-hydroxyl ketones or 2,3-dihydroxyl esters (Scheme 1a,b), while the catalytic asymmetric construction of 2,3-dihydroxyl carbonyl compounds has yet to be explored. The direct catalytic asymmetric aldol addition of hydroxyacetone to arylglyoxals is an ideal transformation that can be anticipated to construct such 2,3-dihydroxyl-1,4-carbonyl units (Scheme 1c). We report a chiral primary amine-catalyzed direct organocatalytic asymmetric aldol reaction of arylglyoxals with hydroxyacetone, which afforded chiral 2,3-dihydroxy-1,4-diones in high yields with good to excellent diastereoselectivities and excellent enantioselectivities.
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