Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids
Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids
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DOI：
10.1248/cpb.c15-00983
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发表时间：
2016-07-01
影响因子：
1.7
通讯作者：
Takemoto, Yoshiji
中科院分区：
文献类型：
--
作者：
Hayama, Noboru;Azuma, Takumi;Takemoto, Yoshiji
通过一种新型的带有手性氨基噻吩的芳基硼酸实现了第一次氮亲核试剂与α，β-不饱和羧酸的分子间不对称Michael加成。使用BnONH 2作为亲核试剂以良好的产率和高对映体选择性（高达90%产率，97%对映体过量（ee））得到一系列对映体富集的β-（苄氧基）氨基酸衍生物。所获得的产物被有效地转化为光学活性的β-氨基酸和1，2-二胺衍生物。
The first intermolecular asymmetric Michael addition of nitrogen-nucleophiles to alpha,beta-unsaturated carboxylic acids was achieved through a new type of arylboronic acid equipped with chiral aminothiourea. The use of BnONH2 as a nucleophile gives a range of enantioenriched beta-(benzyloxy)amino acid derivatives in good yields and with high enantioselectivity (up to 90% yield, 97% enantiomeric excess (ee)). The obtained products are efficiently converted to optically active beta-amino acid and 1,2-diamine derivatives.