氨甲酰基硅烷与醛反应直接合成α-羟基酰胺
收稿日期: 2014-06-23
修回日期: 2014-09-10
网络出版日期: 2014-09-25
基金资助
山西省留学回国人员基金(No. 0713)、山西省自然科学基金(No. 2012011046-9)、山西师范大学基金(No. SD2014CXXM-53)资助项目.
Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes
Received date: 2014-06-23
Revised date: 2014-09-10
Online published: 2014-09-25
Supported by
Project supported by the Shanxi Province Foundation for Returness Overseas Scientists of China (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of Shanxi Normal University (No. SD2014CXXM-53).
姚远 , 李伟东 , 仝文婷 , 陈建新 . 氨甲酰基硅烷与醛反应直接合成α-羟基酰胺[J]. 有机化学, 2015 , 35(1) : 223 -227 . DOI: 10.6023/cjoc201408006
α-Hydroxyamides are directly synthesized by the reaction of N,N-dimethylcarbamoyl(trimethyl)silane with various aldehydes. Most of yields are 71%～91%. Their structures were confirmed by 1H NMR, 13C NMR, IR and elemental analysis. Through carbamoylsilane reacted with the variety of aldehydes, the results indicated that the electronic effect was an important factor in the addition reaction, which influenced on the rate and yields of the reaction. A reaction mechanism is proposed. The main advantages of the developed methodology are mild reaction conditions, less byproducts, high yields of products and simple work-up procedure. An effective synthesis method of α-hydroxyamides has been developed.
Key words： nucleophilic addition; carbamoylsilane; α-hydroxyamides; aldehydes; carbenes
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