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Asymmetric 1,3-Dioxane Synthesis by Using Bifunctional Thiourea Catalysis
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DOI：10.1002/asia.70698.png)
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Abstract
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The hemiacetalization/oxy-Michael addition cascade reaction of delta-hydroxy-alpha,beta-unsaturated carbonyl compounds forming 1,3-dioxanes is known to be an efficient method for the stereoselective synthesis of optically active 1,3-diol structures, which are found in a number of pharmaceutically-relevant compounds. However, to date, no catalytic enantioselective reactions using carboxylic acid derivatives as Michael acceptors have been reported. In this study, a catalytic asymmetric hemiketalization/oxy-Michael addition cascade reaction was developed using phenyl trifluoromethyl ketone as the carbonyl reagent and chiral bifunctional thiourea catalysts. The reaction proceeded in good yields with high enantio- and diastereoselectivity. This method is applicable not only to delta-hydroxy-alpha,beta-unsaturated ketones but also to carboxylic acid derivatives, thereby leading to synthetic flexibility based on high oxidation states.
Keywords:
1,3-dioxane
bifunctional thiourea catalyst
enantioselective synthesis
trifluoromethyl ketone
alpha,beta-unsaturated carboxylic acid derivative
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