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Highly Enantioselective Synthesis of Pseudo-C2-Symmetric Axially Chiral Biaryl Diphosphines via Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition

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School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne NE1 7RU, U.K.
* To whom correspondence should be addressed. E-mail: [email protected]
Cite this: Organometallics 2008, 27, 19, 4837–4840
Publication Date (Web):September 13, 2008
https://doi.org/10.1021/om800755x
Copyright © 2008 American Chemical Society
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Abstract

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Cationic rhodium complexes based on (R)-BINAP catalyze the sequential double [2 + 2 + 2] cycloaddition between 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne and an internal 2,n-diyne followed by its terminal counterpart in an operationally straightforward procedure to afford pseudo-C2-symmetric axially chiral biaryl diphosphines in good yield and with exceptionally high enantioselectivity.

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Full details of experimental procedures and characterization data for all compounds, and for compounds 3a and 4, tables and CIF files giving details of crystal data, structure solution and refinement, atomic coordinates, bond distances, bond angles, and anisotropic displacement parameters. This material is available free of charge via the Internet at http://pubs.acs.org.

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  39. Simon Doherty, Catherine H. Smyth, Ross W. Harrington, William Clegg. ChemInform Abstract: Highly Enantioselective Synthesis of Pseudo-C 2 -Symmetric Axially Chiral Biaryl Diphosphines via Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition.. ChemInform 2009, 40 (5) https://doi.org/10.1002/chin.200905195

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