化学
克莱森重排
电泳剂
磺酰
烯丙基重排
催化作用
铑
立体选择性
不对称诱导
芳基
立体化学
重排反应
对映选择合成
组合化学
药物化学
有机化学
烷基
作者
Yun Liu,Yushuang Chen,Aying Yihuo,Yuqiao Zhou,Xiaohua Liu,Lili Lin,Xiaoming Feng
标识
DOI:10.1021/acscatal.1c05789
摘要
A tandem asymmetric catalytic O–H insertion/Barnes–Claisen rearrangement reaction from 4-acyl-1-sulfonyl-1,2,3-triazoles with allylic alcohols is developed for the purpose of synthesizing all possible stereomers of α-aminoketones under mild conditions. It is found that 4-acyl-1-sulfonyl-1,2,3-triazoles not only form rhodium carbenoids with higher electrophilicity under milder conditions in comparison to 4-aryl-1-sulfonyl-1,2,3-triazoles but also afford another coordination model during the N,N′-dioxide/metal complex promoted asymmetric Barnes–Claisen rearrangement. In addition, two different O–H insertion intermediates have been separated and their transformations have been researched. On the basis of control experiments and previous works, a possible mechanism is proposed to illustrate the reaction process and the induction of the stereoselectivity.
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