It is well known that incorporation of fluorine atoms into target molecules can modify their chemical and biological properties. For this reason, the synthesis of mono- and trifluoromethylated compounds has recently received synthetic interest for the preparation of pharmaceuticals and agrochemicals as well as for their use in different scientific fields such as material sciences, agriculture and organic chemistry. In this lecture, we report our findings concerning the preparation of chiral fluorinated g-monosubstituted and g,g-disubstituted butenolides and butyrolactams through a diastereoselective Mukaiyama-Mannich reaction between heterocyclic silyloxy dienes and fluorinated aldimines having a N-tert-butanesulfinyl group as chiral auxiliary. On the other hand, intramolecular enyne metathesis has widely been used alone or in combination with a Diels-Alder reaction to prepare various interesting synthetic and natural products including amino acids, heterocycles etc. This reaction is considered a very powerful tool in organic synthesis as it allows the economical formation of cyclic functionalized products.However, there are only few examples of ring-closing enyne metathesis (RCEYM) using fluorinated derivatives in the literature. In the final part of the lecture, we describe a simple methodology for the synthesis of a new family of monofluorinated dienes obtained by RCEYM of fluorinated enynes, which proved to be efficient substrates in a Diels-Alder reaction to afford carbo- and heterocycle derivatives.

Strategies for the synthesis of simple mono- and trifluoromethylated  scaffolds

2019 Spring National Meeting

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