Literature DB >> 15527296

Monomeric cobalt oxazoline palladacycles (COP). Useful catalysts for catalytic asymmetric rearrangement of allylic trichloroacetimidates.

Stefan F Kirsch1, Larry E Overman, Mary P Watson.   

Abstract

Cobalt oxazoline palladacycles (COP) containing acetylacetonate and hexafluoroacetylacetonate ligands were prepared as catalysts for the asymmetric rearrangement of allylic trichloroacetimidates. These monomeric catalysts are more soluble than the previously described chloride-bridged dimer COP-Cl (1). COP-hfacac (2) provides rearranged allylic trichloroacetamides with high enantiomeric purities (91-98% ee) in solvents of widely varying polarities: cyclohexane, toluene, 1,2-dichloroethane, ethyl acetate, acetone, acetonitrile, and THF. The first single-crystal X-ray structure of a COP catalyst is also reported.

Entities:  

Year:  2004        PMID: 15527296     DOI: 10.1021/jo0487092

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  9 in total

1.  Molecular Rearrangements in the Construction of Complex Molecules.

Authors:  Larry E Overman
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Catalytic asymmetric synthesis of chiral allylic esters.

Authors:  Stefan F Kirsch; Larry E Overman
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

3.  Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors:  Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2018-01-10       Impact factor: 15.419

4.  Catalytic Asymmetric Synthesis of Branched Chiral Allylic Phenyl Ethers from (E)-Allylic Alcohols.

Authors:  Angela C Olson; Larry E Overman; Helen F Sneddon; Joseph W Ziller
Journal:  Adv Synth Catal       Date:  2009-12       Impact factor: 5.837

5.  Mechanism of the cobalt oxazoline palladacycle (COP)-catalyzed asymmetric synthesis of allylic esters.

Authors:  Jeffrey S Cannon; Stefan F Kirsch; Larry E Overman; Helen F Sneddon
Journal:  J Am Chem Soc       Date:  2010-11-03       Impact factor: 15.419

6.  Asymmetric Synthesis of (+)-Iso-6-Cassine via Stereoselective Intramolecular Amidomercuration.

Authors:  Satwinder Singh; Om V Singh; Hyunsoo Han
Journal:  Tetrahedron Lett       Date:  2007-11-19       Impact factor: 2.415

7.  Catalytic asymmetric synthesis of allylic thiol derivatives.

Authors:  Larry E Overman; Scott W Roberts; Helen F Sneddon
Journal:  Org Lett       Date:  2008-03-13       Impact factor: 6.005

8.  Highly efficient gold(I)-catalyzed Overman rearrangement in water.

Authors:  Dong Xing; Dan Yang
Journal:  Beilstein J Org Chem       Date:  2011-06-08       Impact factor: 2.883

9.  Enantioselective synthesis and application to the allylic imidate rearrangement of amine-coordinated palladacycle catalysts of cobalt sandwich complexes.

Authors:  Doyle J Cassar; Gennadiy Ilyashenko; Muhammad Ismail; James Woods; David L Hughes; Christopher J Richards
Journal:  Chemistry       Date:  2013-11-21       Impact factor: 5.236

  9 in total

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