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Base-Mediated Stereospecific Synthesis of Aryloxy and Amino Substituted Ethyl Acrylates

Author:
Kabir, M. Shahjahan, Namjoshi, Ojas A., Verma, Ranjit, Lorenz, Michael, Phani Babu Tiruveedhula, V. V. N., Monte, Aaron, Bertz, Steven H., Schwabacher, Alan W., Cook, James M.
Source:
Journal of organic chemistry 2012 v.77 no.1 pp. 300-310
ISSN:
1520-6904
Subject:
Lewis bases, acrylates, chemical structure, cross-coupling reactions, heterocyclic nitrogen compounds, industry, organic chemistry, phenols, polymers, screening, stereoselectivity
Abstract:
The stereospecific synthesis of aryloxy and amino substituted E- and Z-ethyl-3-acrylates is of interest because of their potential in the polymer industry and in medicinal chemistry. During work on a copper-catalyzed cross-coupling reaction of ethyl (E)- and (Z)-3-iodoacrylates with phenols and N-heterocycles, we discovered a very simple (nonmetallic) method for the stereospecific synthesis of aryloxy and amino substituted acrylates. To study this long-standing problem on the stereoselectivity of aryloxy and amino substituted acrylates, a series of O- and N-substituted nucleophiles was allowed to react with ethyl (E)- and (Z)-3-iodoacrylates. Screening of different bases indicated that DABCO (1,4-diazabicyclo[2.2.2]octane) afforded successful conversion of ethyl (E)- and (Z)-3-iodoacrylates into aryloxy and amino substituted ethyl acrylates in a stereospecific manner. Herein are the details of this DABCO-mediated stereospecific synthesis of aryloxy and amino substituted E- or Z-acrylates.
Agid:
5498647