化学
产量(工程)
立体选择性
硅烷
烯醇
迈克尔反应
化学计量学
差向异构体
催化作用
对映体
配体(生物化学)
药物化学
有机化学
材料科学
冶金
生物化学
受体
作者
Ryoji Sugiyama,Masahisa Nakada
出处
期刊:Synlett
[Georg Thieme Verlag KG]
日期:2023-02-08
卷期号:34 (11): 1235-1240
被引量:1
摘要
Abstract A highly enantio- and diastereoselective Mukaiyama–Michael reaction of 2-(phenylsulfonyl)cyclopent-2-en-1-one by using an enol silane of tert-butyl thiopropionate is described. The product was formed in 87% yield with a dr of 27:1 and 91% ee under stoichiometric conditions, whereas the yield, dr, and ee were 89%, 49:1, and 88% ee, respectively, under catalytic conditions. A highly stereoselective epimerization of the product of the Mukaiyama–Michael reaction which proceeds in 77% yield with a dr of 22:1 is also described. Because both enantiomers of the ligand for this Mukaiyama–Michael reaction are available, a method for the synthesis of all four stereoisomers of the product as useful chiral building blocks has been established.
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