Preparation of E-1,3-diaminoethenyl functional groups by the reaction of enol tosylate of alpha-formylglycine with primary and secondary amines

Article history: Received October 21, 2015 Received in revised form December 20, 2015 Accepted 12 January 2016 Available online 14 January 2016 The E-1,3-diaminoethenyl functional group is a potentially useful synthon. A number of examples of E-1,3-diaminoethenyl functional groups were prepared in good yield starting from an E-enol tosylate of a serine based diketopiperazine and 1°or 2° amine nucleophiles. The reaction proceeds via a stereoselective nucleophilic substitution pathway. © 2016 Growing Science Ltd. All rights reserved.