Issue 8, 2016
From the journal:

Chemical Communications

Catalytic asymmetric conjugate addition of isocyanoacetate to (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor†

Claudia Del Fiandra,a   Maria Moccia,b   Valentina Cerullia  and  Mauro F. A. Adamo*a  

* Corresponding authors

a Centre for Synthesis and Chemical Biology (CSCB), Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland
E-mail: madamo@rcsi.ie
Fax: (+353) 1 4022168

b National Research Council, Institute of Crystallography, Via G. Amendola 122/O, 70126 Bari, Italy

Abstract

(Z)-3-Substituted-2-(4-pyridyl)-acrylonitriles, a reactive class of Michael acceptors obtained exclusively as a single (Z) isomer, reacted with un-substituted isocyanoacetate esters mediated by phase-transfer catalysis to give, after base promoted cyclisation, functionalized imines in up to 94% ee and as a single diastereoisomer.

Graphical abstract: Catalytic asymmetric conjugate addition of isocyanoacetate to (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor

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Article information

DOI
https://doi.org/10.1039/C5CC08105J
Article type
Communication
Submitted
28 Sep 2015
Accepted
02 Dec 2015
First published
02 Dec 2015

Chem. Commun., 2016,52, 1697-1700

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Catalytic asymmetric conjugate addition of isocyanoacetate to (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor

C. Del Fiandra, M. Moccia, V. Cerulli and M. F. A. Adamo, Chem. Commun., 2016, 52, 1697 DOI: 10.1039/C5CC08105J

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