Planar Chiral Phosphoramidites with a Paracyclophane Scaffold: Synthesis, Gold(I) Complexes, and Enantioselective Cycloisomerization of Dienynes
| Autor: | Arnaud Voituriez, Jean-François Betzer, Kévin Isaac, Angela Marinetti, Pascal Retailleau, Zhiyong Wu |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2015 |
| Předmět: |
Phosphoramidite
Bicyclic molecule 010405 organic chemistry Chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Aryl Organic Chemistry Enantioselective synthesis General Chemistry Planar chirality 010402 general chemistry 01 natural sciences Heptene Catalysis 0104 chemical sciences 3. Good health Stereocenter chemistry.chemical_compound Cycloisomerization |
| Zdroj: | Chemistry-A European Journal Chemistry-A European Journal, Wiley-VCH Verlag, 2016, 22 (10), pp.3278-3281. ⟨10.1002/chem.201504658⟩ |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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