Beilstein J. Org. Chem.2007,3, No. 28, doi:10.1186/1860-5397-3-28
functionality, in both cases at a terminal carbon atom of 2.
All attempts to achieve a one-step cyclization according to Scheme 1 starting from glycine or from phenylglycine seemed to fail under various reaction conditions (for instance one equiv. of NaOH, K2CO3 or triethylamine in water), regularly giving rise
to solid, presumably oligomeric material, insoluble even in DMSO.
We therefore tested the stepwise, controlled synthesis of products of type 3a with glycidyl esters of N-acyl [6] and N-tosyl glycine and phenylglycine as isolated key intermediates: under basic reaction conditions (NaH, sec-BuLi or LDA
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Graphical Abstract
Scheme 1:
Planned construction for morpholinones 3 from amino acid and glycidyl derivatives 1 and 2. R1, R3 =...