化学
立体选择性
氢解
区域选择性
顺反异构
立体化学
光延反应
偶氮二甲酸二乙酯
键裂
药物化学
有机化学
催化作用
三苯基膦
作者
Mario Ordóñez,Rubén Oswaldo Argüello‐Velasco,Iván Romero‐Estudillo,Victoria Labastida‐Galván,Teodoro Miranda-Blancas
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2023-08-31
卷期号:55 (24): 4181-4190
摘要
Abstract We report a practical method for the first stereoselective synthesis of diethyl cis- and trans-(4-hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phosphonates, as well as ethyl cis- and trans-(4-hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phenylphosphinates. The main feature of this method is the regioselective 1,4-phosponylation to N-Cbz quinolin-4(1H)-one using diethyl phosphite or ethyl phenylphosphinate followed by a highly diastereoselective reduction to give the cis stereoisomers as favored products, which were converted into trans stereoisomers through the Mitsunobu reaction. Cleavage of the N-Cbz bond under hydrogenolysis gave the target heterocyclic α-aminophosphonates and α-aminophosphinates.
科研通智能强力驱动
Strongly Powered by AbleSci AI