使用手性多功能硫脲催化剂对α,β-不饱和羧酸进行溶剂依赖性手性可切换硫杂迈克尔加成反应。
A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst.
作者信息
Hayama Noboru, Kobayashi Yusuke, Sekimoto Eriko, Miyazaki Anna, Inamoto Kiyofumi, Kimachi Tetsutaro, Takemoto Yoshiji
机构信息
Graduate School of Pharmaceutical Sciences , Kyoto University , Yoshida, Sakyo-ku , Kyoto 606-8501 , Japan . Email:
School of Pharmacy and Pharmaceutical Sciences , Mukogawa Women's University , 11-68, 9-Bancho, Koshien , Nishinomiya , Hyogo 663-8179 , Japan.
出版信息
Chem Sci. 2020 May 14;11(21):5572-5576. doi: 10.1039/d0sc01729a. eCollection 2020 Jun 7.
An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing the solvent. The origin of the chirality switch in the products was examined in each solvent spectroscopic analyses.
报道了一种使用带有芳基硼酸和叔胺部分的硫脲催化剂，将芳基硫醇对α,β-不饱和羧酸进行不对称硫杂迈克尔加成反应。仅仅通过改变溶剂，迈克尔加成产物的两种对映体都可以以高对映选择性和良好的产率得到。通过光谱分析在每种溶剂中研究了产物中手性翻转的起源。
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