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

Mario Ordóñez; Rubén Oswaldo Argüello-Velasco; Teodoro Miranda-Blancas; Ivan Romero-Estudillo; Victoria Labastida-Galván

doi:10.1055/a-2164-2075

Synthesis, Table of Contents

Synthesis 2023; 55(24): 4181-4190
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

Mario Ordóñez ∗

^aCentro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico

,

Rubén Oswaldo Argüello-Velasco∗

^bFacultad de Ciencias Químicas e Ingeniería, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, México

,

Teodoro Miranda-Blancas

^aCentro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico

,

Ivan Romero-Estudillo

^aCentro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico

^cCONAHCYT-Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico

,

Victoria Labastida-Galván

^aCentro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico

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Abstract

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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 reaction

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References

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