An axially chiral N,N-ligand developed from a [1,1′binaphthalene]-2,2′-diol (BINOL)-based skeleton and phenanthroline is found to be capable of promoting Pd-catalyzed asymmetric allylic amination and alkylation of allyl acetates. The reaction is compatible with cyclic and acyclic secondary amines, primary aliphatic amines, malononitrile, and dialkyl malonates, affording the corresponding chiral products in up to 99% yield and with up to >99% enantiomeric excess.
* sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c01972.Detailed experimental procedures, characterization data, and copies of nuclear magnetic resonance (NMR) and HPLC spectra (PDF)■ AUTHOR INFORMATION
Quinolines especially 2-aminoquinolines are highly important heterocycles in medicinal chemistry. 2-Aminoquinolines can be synthesized via stepwise construction of quinoline ring followed by additional amination, however the protocol is cumbersome. Herein, we describe a [5+1] cyclization of 2-vinylanilines with tetraalkylthiuram disulfide in the presence of iodine and copper(II) triflate. This reaction directly employs readily available and low-cost thiuram as both C1 synthon and nitrogen source, providing a facile approach for one-step synthesis of a variety of 2-aminoquinolines in good to excellent yields.
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