Michael Guillot* , Olivier Riant Tom Leyssens
The development of green chemical processes has gained increasing importance since the introduction of the concept 21 years ago. Green alternatives are even more important when speaking of enantiopure synthesis. However, developing an efficient green process comes with obstacles, especially when one wants to carry out SN2 reactions in water. In this paper, we developed and optimized a 2-step stereospecific synthesis starting from L-Phenylalanine and yielding (R)-2-(1H-1, 2, 4-triazol-1-yl)-3-phenylpropanoic acid ((R)-BnTAA), involving a total of 3 SN2 reactions. The reaction was designed to minimize waste production and match other green chemistry criteria. The reaction was studied by H1NMR in order to maximize efficiency. In the end, we present a green process with a minimized waste production and a total yield of 56%.
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