Direct Asymmetric Aldol Reaction of 5H-Oxazol-4-ones with Aldehydes Catalyzed by Chiral Guanidines
Direct Asymmetric Aldol Reaction of 5H-Oxazol-4-ones with Aldehydes Catalyzed by Chiral Guanidines
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DOI：
10.1021/ja101216x
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发表时间：
2010-05-12
影响因子：
15
通讯作者：
Sugimura, Takashi
中科院分区：
文献类型：
--
作者：
Misaki, Tomonori;Takimoto, Gouta;Sugimura, Takashi
研究了一种新的手性双环胍催化的5 H-恶唑-4-酮与醛的直接羟醛缩合反应。本发明的羟醛缩合反应使用在适当位置带有羟基的双环胍以高对映选择性顺利进行，并且5 H-恶唑-4-酮和醛的各种组合是适用的。该方法提供了在α-碳原子上带有手性季立体中心的合成有用的α，β-二羟基羧酸酯。
A new chiral bicyclic guanidine-catalyzed direct catalytic aldol reaction of 5H-oxazol-4-ones with aldehydes has been developed. The present aldol reaction proceeds smoothly with high enantioselectivity using bicyclic guanidines bearing a hydroxy group at the appropriate position, and various combinations of 5H-oxazol-4-ones and aldehydes are applicable. The method provides synthetically useful alpha,beta-dihydroxycarboxylates bearing a chiral quaternary stereogenic center at the alpha-carbon atom.