A Convenient Synthesis of Some Phenyl‐Substituted Aliyclic β‐Amino Esters and β‐Lactams

Author:

Nonn Melinda1,Drahos László2,Kiss Loránd3ORCID

Affiliation:

1. MTA TTK Lendület Artificial Transporter Research Group Institute of Materials and Environmental Chemistry HUN-REN Research Centre for Natural Sciences Magyar tudósok krt. 2 H-1117 Budapest Hungary

2. Institute of Organic Chemistry, MS Proteomics Research Group HUN-REN Research Centre for Natural Sciences Magyar tudósok krt. 2 H-1117 Budapest Hungary

3. Institute of Organic Chemistry, Stereochemistry Research Group HUN-REN Research Centre for Natural Sciences Magyar tudósok krt. 2 H-1117 Budapest Hungary

Abstract

AbstractA convenient synthetic procedure has been developed for the access of phenyl‐substituted alicyclic β‐amino acid derivatives. The substrate‐directed palladium‐catalyzed cross‐coupling of phenylboronic acid with five‐ or six‐membered cycloalkene β‐amino esters and bicyclic β‐lactams in the presence of Selectfluor as oxidant provided phenyl‐substituted alicyclic β‐amino esters and azetidin‐2‐ones. Phenylations were investigated under various experimental conditions with different ligands and solvent systems. The structural architecture of the starting compounds and the position of their ring olefin bond influenced and predetermined the structure of the products.

Funder

European Commission

Publisher

Wiley

Subject

General Chemistry

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