Planar Chiral Phosphoramidites with a Paracyclophane Scaffold: Synthesis, Gold(I) Complexes, and Enantioselective Cycloisomerization of Dienynes

Zhiyong Wu (1) , Kevin Isaac (1) , Pascal ́ Retailleau (1) , Jean-François Betzer (1) , Arnaud Voituriez (1) , Angela Marinetti (1)

1 ICSN - Institut de Chimie des Substances Naturelles

The key structuralf eature of the new phosphor-amidites is ap aracyclophane scaffoldi nw hich two aryl rings are tethered by both a1 ,8-biphenylene unit and aO ÀPÀOb ridge. Suitable aryl substituents generate planar chirality.T he corresponding gold(I) complexes promote the cycloisomerization of prochiral nitrogen-tethered dienynes. These reactions afford bicyclo[4.1.0]hep-tene derivatives displaying three contiguous stereogenic centers, with very high diastereoselectivity and up to 95 % ee.

Domaines: Chimie organique

Zhiyong Wu, Kevin Isaac, Pascal ́ Retailleau, Jean-François Betzer, Arnaud Voituriez, et al.. Planar Chiral Phosphoramidites with a Paracyclophane Scaffold: Synthesis, Gold(I) Complexes, and Enantioselective Cycloisomerization of Dienynes. Chemistry - A European Journal, 2016, 22 (10), pp.3278-3281. ⟨10.1002/chem.201504658⟩. ⟨hal-02152297⟩