PMID: 11925230Apr 2, 2002Paper

Novel chiral biferrocene ligands for palladium-catalyzed allylic substitution reactions

The Journal of Organic Chemistry
Li XiaoMichael Widhalm

Abstract

Eleven novel aminophosphine ligands have been synthesized, all of which contain a chiral 2,2' '-bridged biferroceno unit as part of a biferrocenoazepine substructure. The efficiency of these compounds as chiral auxiliaries in palladium-mediated allylic substitution reactions has been investigated. Depending on the degree of (steric) fit between proper ligands and cyclic or noncyclic substrates, reactions with 46-87% ee were achieved. The molecular structure of a palladium dichloride complex of one of the ligands was determined by X-ray diffraction and compared to its binaphthyl analogue. In the solid state, the azepine substructure of these two complexes adopts totally different conformations with either local C(2) (binaphthyl) or local C(1) (biferrocene derivative) symmetry. These structural changes are well-reproduced by empirical force field calculations and are also reflected in significantly different behavior in asymmetric catalysis.

References

Feb 1, 1996·Chemical Reviews·Barry M. Trost, David L. Van Vranken

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Citations

Feb 1, 2006·Chemical Communications : Chem Comm·Myung-Jong JinYoung-Mok Kim
Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Yaping WangKurt Mereiter
Nov 10, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Keishiro TaharaJun-ichi Kikuchi
May 16, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Keishiro TaharaJun-ichi Kikuchi
Mar 6, 2021·Acta Crystallographica. Section C, Structural Chemistry·Philipp HoneggerMichael Widhalm

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