Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide
Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide
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DOI：
10.1021/acs.joc.8b00743
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发表时间：
2018-05-18
影响因子：
3.6
通讯作者：
Shibasaki, Masakatsu
中科院分区：
文献类型：
--
作者：
Takeuchi, Toshifumi;Kumagai, Naoya;Shibasaki, Masakatsu
在酸碱协同催化剂的催化下，以立体发散的方式促进了-乙烯基- 7-氮唑啉酰胺在芳香和脂肪醛上的不对称醛醇加成反应。关键的结构元素，7-氮唑啉部分，促进催化烯醇化，允许随后的立体选择性醛醇加成。对映选择性合成了蓝草内酯C和肉桂酸的关键中间体，支持了该方案的合成效用。
A direct catalytic asymmetric aldol addition of an alpha-vinyl 7-azaindoline amide to both aromatic and aliphatic aldehydes was promoted by a cooperative acid/base catalyst in a stereodivergent manner. The key structural element, a 7-azaindoline moiety, facilitated catalytic enolization, allowing for subsequent stereoselective aldol addition. Enantioselective synthesis of the key intermediate of blumiolide C and kainic acid supported the synthetic utility of this protocol.