This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines based on the aza-Michael addition of primary amines to 3,4-difunctionalized-1,3-diene followed by an intramolecular cyclization.
We report a new procedure for highly stereoselective synthesis of difunctionalized allyl and vinyl bromides E-4 and E-5 via a tandem reaction of bromination-dehydrobromination of tetraethyl prop-2-ene-1,2-diyldiphosphonate in the presence of DBU in acetonitrile at room temperature. The coupling reaction of allyl bromide E-4 with various primary amines in methanol at 0 °C, followed by S N 2' reaction, provides a new family of tetraethyl 1-(alkylamino)prop-2-ene-1,2-diyldiphosphonates 6 in high yields.
An efficient and straightforward approach toward functionalized allylic amines and ethers is disclosed starting from tetraethyl (3-bromoprop-1-ene-1,2-diyl)bisphosphonate (E)-1 and secondary and tertiary amines. The coupling reaction of allyl bromide (E)-1 with less bulky secondary amines provides a new family of allylamines 3, while, its reaction with more bulky secondary and tertiary amines, in methanol at reflux, led to functional allyl ethers 4 and 5.
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