Chiral 1,2-diaminocyclohexane as organocatalyst for enantioselective aldol reaction |
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Authors: | Yi LiuJunfeng Wang Qi Sun Runtao Li |
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Institution: | State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China |
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Abstract: | A simple and commercially available chiral 1,2-diaminocyclohexane as catalyst, hexanedioic acid as co-catalyst could efficiently catalyze the asymmetric aldol reaction in MeOH-H2O. Cyclic ketones as aldol substrates gave the anti-β-hydroxyketone products with moderate to good yields, diastereoselectivity and enantioselectivity (up to 78% yield, >20:1 anti/syn, 94% ee). Hydroxyacetone as aldol substrate afforded the syn-α, β-dihydroxyketones as major products in up to 85% yield with good enantioselectivity (up to >20:1 syn/anti, 93% ee). |
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Keywords: | Asymmetric aldol reaction Diaminocyclohexane Organocatalyst Hydroxyketone |
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