Planar Chiral Phosphoramidites with a Paracyclophane Scaffold: Synthesis, Gold(I) Complexes, and Enantioselective Cycloisomerization of Dienynes - Archive ouverte HAL
Article Dans Une Revue Chemistry - A European Journal Année : 2016

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

Résumé

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
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Dates et versions

hal-02152297 , version 1 (20-09-2019)

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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⟩
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