Planar Chiral Phosphoramidites with a Paracyclophane Scaffold: Synthesis,Gold(I) Complexes,and Enantioselective Cycloisomerization of Dienynes |
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| Authors: | Zhiyong Wu Kévin Isaac Dr Pascal Retailleau Dr Jean‐François Betzer Dr Arnaud Voituriez Dr Angela Marinetti |
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| Institution: | Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Gif-sur-Yvette, France |
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| Abstract: | The key structural feature of the new phosphoramidites is a paracyclophane scaffold in which two aryl rings are tethered by both a 1,8‐biphenylene unit and a O?P?O bridge. Suitable aryl substituents generate planar chirality. The corresponding gold(I) complexes promote the cycloisomerization of prochiral nitrogen‐tethered dienynes. These reactions afford bicyclo4.1.0]heptene derivatives displaying three contiguous stereogenic centers, with very high diastereoselectivity and up to 95 % ee. |
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| Keywords: | cycloisomerization enantioselectivity gold catalysis phosphoramidite planar chirality |
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