Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

[Display omitted] The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and sepa...

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Bibliographic Details
Published in:Tetrahedron letters 2005-05, Vol.46 (22), p.3843-3846
Main Authors: Gorobets, Evgueni, Wheatley, Bronwen M.M., Hopkins, J. Matthew, McDonald, Robert, Keay, Brian A.
Format: Article
Language:English
Subjects:
BIPHEP derivatives
Ullmann coupling
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Summary:[Display omitted] The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of 1 (R = O tBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3′-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.03.183