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Synthesis 2023; 55(24): 4181-4190
DOI: 10.1055/a-2164-2075
DOI: 10.1055/a-2164-2075
paper
First Stereoselective Synthesis of Diethyl cis- and trans-(4-Hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phosphonates and Ethyl Phenylphosphinates from Quinolin-4(1H)-one
The authors thank the Consejo Nacional de Humanidades Ciencias y Tecnologías (CONAHCYT) for financial support through projects 286614, 140607, 807 and Investigadores por México contract 942. R.O.A.V. and T.M.B. wish to thank CONAHCYT for Graduate Scholarships 332980 and 971500. The authors thank to Laboratorio Nacional de Estructura de Macromoléculas (CONAHCYT 315896) for the spectroscopic analyses.
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.
Key words
heterocyclic α-aminophosphonates - α-aminophosphinates - 1,4-addition - diastereoselective reduction - Mitsunobu reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2106-1461.
- Supporting Information
Publication History
Received: 05 August 2023
Accepted after revision: 31 August 2023
Accepted Manuscript online:
31 August 2023
Article published online:
13 October 2023
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