A Dual Arylboronic Acid-Aminothiourea Catalytic System for the Asymmetric Intramlecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids
A Dual Arylboronic Acid-Aminothiourea Catalytic System for the Asymmetric Intramlecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids
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DOI：
10.1021/ol501954r
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发表时间：
2014-08-15
期刊：
影响因子：
5.2
通讯作者：
Takemoto, Yoshiji
中科院分区：
文献类型：
--
作者：
Azuma, Takumi;Murata, Akihiro;Takemoto, Yoshiji
一种双官能团的氨基硼酸首次被用来促进α，β-不饱和羧酸的分子内氮杂和氧杂-迈克尔反应。芳基硼加成与手性氨基硫脲的结合使得这些反应能够以对映选择性的方式成功地进行，以高产率和ee‘s(高达96%ee)提供所需的杂环。通过一锅法对映体选择性地合成(+)-红球菌胺B，证明了这种双重催化体系的整体用途。
A bifunctional aminoboronic acid has been used to facilitate for the first time the intramolecular aza- and oxa-Michael reactions of alpha,beta-unsaturated carboxylic acids. The combination of an arylboronic add with a chiral aminothiourea allowed for these reactions to proceed successfully in an enantioselective manner to afford the desired heterocycles in high yields and ee's (up to 96% ee). The overall utility of this dual catalytic system was demonstrated by a one-pot enantioselective synthesis of (+)-erythrococcamide B, which proceeded via sequential Michael and amidation reactions.