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1 article(s) from Barkov, Alexey Yu.

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

Marina Rubina,
William M. Sherrill,
Alexey Yu. Barkov and
Michael Rubin

Beilstein J. Org. Chem. 2014, 10, 1536–1548, doi:10.3762/bjoc.10.158

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Graphical Abstract

Scheme 1: Intermolecular asymmetric Heck reaction by Hayashi [16].

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Scheme 2: Mechanistic rationale of asymmetric Heck reaction.

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Figure 1: Chiral diphosphine ligands used for intermolecular asymmetric Heck reaction.

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Figure 2: Chiral phosphanyl-oxazoline (PHOX) ligands used for intermolecular asymmetric Heck reaction.

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Scheme 3: Synthetic scheme for preparation of PHOX ligands with chiral cyclopropyl backbone.

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Figure 3: PHOX ligands with chiral cyclopropyl backbone employed in this study.

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Scheme 4: Conformational equilibrium in cationic arylpalladium(II) complexes with chiral ligand L1.

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Figure 4: X-ray structures of complexes (L1)PdCl₂ (left) and (L4)PdCl₂ (right). These structures were origina...

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Scheme 5: For discussion on asymmetric induction imparted by chiral ligands L1 and L2 (originally published i...

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Scheme 6: For discussion on asymmetric induction imparted by chiral ligands L3 (originally published in [64]).

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Scheme 7: Conformational equilibrium in cationic arylpalladium(II) complexes with chiral ligand L4.

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Scheme 8: For discussion on asymmetric induction imparted by chiral ligands L4 (originally published in [64]).

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Scheme 9: Mechanism of migration of C=C double bond leading to isomerization of product 3 into product 4.

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Scheme 10: For discussion on isomerization 3→4 imparted by Pd/L1 complex (originally published in [64]).

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Scheme 11: For discussion on isomerization 3→4 imparted by Pd/L4 complex (originally published in [64]).

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Published 07 Jul 2014

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