Literature DB >> 10891052

Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

B L Feringa1.   

Abstract

The development of an efficient catalytic system for enantioselective carbon-carbon bond formation by 1,4-addition of organometallic reagents (organolithium, Grignard, and organozinc reagents) to enones is a major challenge in organic synthesis. This Account presents the breakthrough realized in this field using chiral phosphoramidite ligands for copper-catalyzed dialkylzinc additions. Applications in catalytic routes to cycloalkanones as well as tandem and annulation procedures with excellent enantioselectivities are discussed.

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Year:  2000        PMID: 10891052     DOI: 10.1021/ar990084k

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  53 in total

1.  Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

Authors:  Venukrishnan Komanduri; Fernando Pedraza; Michael J Krische
Journal:  Adv Synth Catal       Date:  2008-07-07       Impact factor: 5.837

2.  Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates.

Authors:  Xinfang Xu; Wen-Hao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-31       Impact factor: 15.336

3.  Enantioselective construction of pyrrolidines by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethane with imines.

Authors:  Barry M Trost; Steven M Silverman
Journal:  J Am Chem Soc       Date:  2012-03-02       Impact factor: 15.419

4.  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

5.  Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones.

Authors:  Laura A Brozek; Joshua D Sieber; James P Morken
Journal:  Org Lett       Date:  2011-02-02       Impact factor: 6.005

6.  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

7.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

8.  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

9.  Stereoselective alkylations of chiral nitro imine and nitro hydrazone dianions. Synthesis of enantiomerically enriched 3-substituted 1-nitrocyclohexenes.

Authors:  Scott E Denmark; Jeffrey J Ares
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

10.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

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