Threonine-surfactant organocatalysts for the highly diastereo- and enantioselective direct anti-Mannich reactions of hydroxyacetone |
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| Authors: | Chuanlong Wu Xuebing Ma Shi Li Chao Li |
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| Institution: | College of Chemistry and Chemical Engineering Southwest University, Research Institute of Applied Chemistry Southwest University, Chongqing 400715, China The Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing 400715, China The Key Laboratory of Eco-environments in Three Gorges Reservoir Region Ministry of Education, Chongqing 400715, China |
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| Abstract: | In this work, several new l-threonine derivatives as organocatalysts were synthesized in one step for the first time by the reaction of threonine with acyl chlorides at room temperature in trifluoroacetic acid on a large-scale without protecting groups involved or chromatographic techniques, and those threonine-surfactant organocatalysts mediated the direct asymmetric anti-Mannich reactions of hydroxyacetone and anilines with aldehydes to synthesize anti-1,2-amino alcohols in good yields (75-93%) and highly enantioselectivities (up to 99% ee). |
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