Planar chiral [2.2]paracyclophane-based phosphine-Brønsted acid catalysts bearing exceptionally high reactivity for aza-Morita–Baylis–Hillman reaction

Several new planar chiral bifunctional phosphine compounds based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to the aza-Morita–Baylis–Hillman reaction. An enantiopure phosphine-phenol catalyst bearing an aryl group as a spacer connec...

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Bibliographic Details
Published in:Tetrahedron letters 2013-01, Vol.54 (5), p.384-386
Main Authors: Kitagaki, Shinji, Ohta, Yuu, Takahashi, Ryohei, Komizu, Mika, Mukai, Chisato
Format: Article
Language:English
Subjects:
Aza-Morita–Baylis–Hillman reaction
Cyclophanes
Organocatalysis
Planar chirality
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Summary:Several new planar chiral bifunctional phosphine compounds based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to the aza-Morita–Baylis–Hillman reaction. An enantiopure phosphine-phenol catalyst bearing an aryl group as a spacer connected to a phosphino group exhibited an exceptionally high reactivity (rt, 2–40min) and good enantioselectivity (up to 85% ee).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.11.021