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"Un nouveau ligand dérivé du binol : le (R)-6,6'- bis (trifluorométhanesulfonyl) -1,1'-bi2-naphtol. Synthèse et applications en catalyse asymétrique"

Abstract : BINOL is an efficient chiral ligand widely used in asymmetric reactions. The work of this thesis concerns the synthesis of a new derivative of BINOL, bearing a triflyl group (CF3SO2) one of the strongest electron withdrawing groups and demonstrates its first applications in asymmetric catalysis.
The first part constitutes a bibliographic review on BINOL and its derivatives substituted by electron withdrawing groups in position 3,3' and/or 6,6'. These latter ligands have shown that the presence of this type of group induces strong increases in stereoselectivity and is beneficial for turnover.
The second part presents the synthesis and the characterization of the new (R)-6,6'-bis(trifluorométhanesulfonyl)-1,1'-bi-2-naphthol. Due to the difficulty of the aromatic trifluoromethanesulfonylation, this synthesis has required numerous attempts which we examined before detailing the original route to this ligand that we developed.
The third part describes the first applications of (R)-6,6'-Tf2BINOL in asymmetric catalysis. The results that we have obtained clearly indicate that this ligand, complexed with oxophilic metals such as zirconium or titanium leads to very active organometallic catalysts.
During the characterization and tests of crystallization of the zirconium complex, we isolated a product of which the structure corresponds to an organometallic cluster. This proved to be air-stable and more powerful in the catalysis of the Mannich-type reactions than the complex prepared in situ.
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Submitted on : Tuesday, December 11, 2007 - 11:34:19 AM
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Omar Mouhtady. "Un nouveau ligand dérivé du binol : le (R)-6,6'- bis (trifluorométhanesulfonyl) -1,1'-bi2-naphtol. Synthèse et applications en catalyse asymétrique". Autre. Université Paul Sabatier - Toulouse III, 2007. Français. ⟨tel-00195619⟩

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