Enantioselective Synthesis of Monosaccharide Analogues by Two-Step Sequential Enamine Catalysis: Benzoyloxylation and Aldol Reaction
Enantioselective Synthesis of Monosaccharide Analogues by Two-Step Sequential Enamine Catalysis: Benzoyloxylation and Aldol Reaction
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DOI：
10.1002/ejoc.202000073
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发表时间：
2020-04
影响因子：
2.8
通讯作者：
Mio Shimogaki;Aika Takeshima;T. Kano;K. Maruoka
中科院分区：
文献类型：
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作者：
Mio Shimogaki;Aika Takeshima;T. Kano;K. Maruoka
描述了一种以对映体和非对映体选择性方式合成单糖类似物的有效途径。通过手性仲胺催化的醛的苯甲酰氧基化反应和手性氨基酸催化的α-苯甲酰氧基醛与被保护的二羟基丙酮的羟醛缩合反应，可以构建三个相邻的立体中心，并以优异的对映选择性得到单一的非对映异构体。
An efficient route to synthesize monosaccharide analogues in an enantio‐ and diastereoselective manner is described. Three contiguous stereocenters can be constructed via enantioselective benzoyloxylation of aldehydes using a chiral secondary amine catalyst and a subsequent aldol reaction of the resultingα‐benzoyloxyaldehydes with the protected dihydroxyacetones using chiral amino acid catalysts, and single diastereomers were obtained with excellent enantioselectivity.