Catalytic Asymmetric Mannich Reactions of Sulfonylacetates
Catalytic Asymmetric Mannich Reactions of Sulfonylacetates
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DOI：
10.1002/anie.200900701
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发表时间：
2009-01-01
影响因子：
16.6
通讯作者：
Ricci, Alfredo
中科院分区：
文献类型：
--
作者：
Cassani, Carlo;Bernardi, Luca;Ricci, Alfredo
芳基磺酰基乙酸酯可以被视为各种α-羧酸根阴离子的合成等价物。相转移催化（PTC）使它们能够温和地去质子化和催化不对称加成到由α-酰胺基砜原位生成的高反应性亚胺（参见方案; Pg=保护基）。产物的合成效用通过其直接转化成一系列β-氨基酸衍生物来证明。
Arylsulfonylacetates can be viewed as synthetic equivalents of a variety of alpha-carboxylate anions. Phase-transfer catalysis (PTC) enabled their mild deprotonation and catalytic asymmetric addition to highly reactive imines generated in situ from alpha-amidosulfones (see scheme; Pg= protecting group). The synthetic utility of the products was demonstrated by their straightforward transformation into a range of beta-amino acid derivatives.