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Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates.

The Journal of organic chemistry (2011-11-15)
M Shahjahan Kabir, Ojas A Namjoshi, Ranjit Verma, Michael Lorenz, V V N Phani Babu Tiruveedhula, Aaron Monte, Steven H Bertz, Alan W Schwabacher, James M Cook
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl acrylate, contains 10-20 ppm MEHQ as inhibitor, 99%
Supelco
Ethyl acrylate, analytical standard
Sigma-Aldrich
Ethyl acrylate, ≥99.5%, stabilized

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