1349709-81-4Relevant articles and documents
Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates
Kabir, M. Shahjahan,Namjoshi, Ojas A.,Verma, Ranjit,Lorenz, Michael,Phani Babu Tiruveedhula,Monte, Aaron,Bertz, Steven H.,Schwabacher, Alan W.,Cook, James M.
experimental part, p. 300 - 310 (2012/03/08)
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.
