Literature DB >> 16802804

Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.

David Martin1, Stefan Kehrli, Magali d'Augustin, Hervé Clavier, Marc Mauduit, Alexandre Alexakis.   

Abstract

The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is unprecedented in conjugate addition, and the additon of the phenyl group, on such enones, cannot be done by other conjugate addition methods.

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Year:  2006        PMID: 16802804     DOI: 10.1021/ja0629920

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  25 in total

1.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

2.  Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters.

Authors:  Kotaro Kikushima; Jeffrey C Holder; Michele Gatti; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2011-04-15       Impact factor: 15.419

3.  Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.

Authors:  Rebecca M Maksymowicz; Philippe M C Roth; Stephen P Fletcher
Journal:  Nat Chem       Date:  2012-07-15       Impact factor: 24.427

4.  Copper-catalyzed asymmetric conjugate addition of alkylzirconium reagents to cyclic enones to form quaternary centers.

Authors:  Philippe M C Roth; Mireia Sidera; Rebecca M Maksymowicz; Stephen P Fletcher
Journal:  Nat Protoc       Date:  2013-12-12       Impact factor: 13.491

5.  Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones.

Authors:  Jeffrey C Holder; Emmett D Goodman; Kotaro Kikushima; Michele Gatti; Alexander N Marziale; Brian M Stoltz
Journal:  Tetrahedron       Date:  2014-11-28       Impact factor: 2.457

6.  Total synthesis of taxane terpenes: cyclase phase.

Authors:  Yoshihiro Ishihara; Abraham Mendoza; Phil S Baran
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

7.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

8.  Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

9.  Enantioselective synthesis of all-carbon quaternary stereogenic centers by catalytic asymmetric conjugate additions of alkyl and aryl aluminum reagents to five-, six-, and seven-membered-ring beta-substituted cyclic enones.

Authors:  Tricia L May; M Kevin Brown; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Stereogenic-at-metal Zn- and Al-based N-heterocyclic carbene (NHC) complexes as bifunctional catalysts in Cu-free enantioselective allylic alkylations.

Authors:  Yunmi Lee; Bo Li; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

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