Literature DB >> 17935094

Enantioselective Tsuji allylations.

Justin T Mohr1, Brian M Stoltz.   

Abstract

The family of allylation reactions developed by Tsuji in the 1980s are capable of generating tertiary and quaternary carbon stereocenters from several synthetic precursors. Despite the utility of these transformations, they have seen little use in the synthesis of natural products. Recently, the power of these reactions was significantly enhanced by the development of enantioselective versions of these transformations. Applications of these methods to the enantioselective syntheses of natural products and pharmaceutical compounds highlight the importance of these developments.

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Year:  2007        PMID: 17935094      PMCID: PMC2967289          DOI: 10.1002/asia.200700183

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  34 in total

1.  Diastereoselective and Enantioselective Palladium-Catalyzed Allylic Substitution with Nonstabilized Ketone Enolates This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We thank Dipl.-Chem. Daniel Ridder for carrying out the crystal structure analyses.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-10-02       Impact factor: 15.336

2.  Total Synthesis of Colombiasin A This work was financially supported by the National Institutes of Health (USA) and The Skaggs Institute for Chemical Biology, postdoctoral fellowships from Bayer AG (to R.K. and W.M.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

Authors:  K. C. Nicolaou; Georgios Vassilikogiannakis; Wolfgang Mägerlein; Remo Kranich
Journal:  Angew Chem Int Ed Engl       Date:  2001-07-02       Impact factor: 15.336

3.  Enantioselective Construction of Quaternary Stereocenters.

Authors:  Jens Christoffers; Alexander Mann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

4.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

5.  A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.

Authors:  Osamu Tokuda; Taichi Kano; Wei-Guo Gao; Tetsuya Ikemoto; Keiji Maruoka
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

6.  Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers.

Authors:  Etienne Bélanger; Katy Cantin; Olivier Messe; Mélanie Tremblay; Jean-François Paquin
Journal:  J Am Chem Soc       Date:  2007-02-07       Impact factor: 15.419

7.  Palladium-catalyzed asymmetric allylic alkylation of alpha-aryl ketones.

Authors:  Barry M Trost; Gretchen M Schroeder; Jesper Kristensen
Journal:  Angew Chem Int Ed Engl       Date:  2002-09-16       Impact factor: 15.336

8.  Palladium-catalyzed synthesis of substituted cycloheptane-1,4-diones by an asymmetric ring-expanding allylation (AREA).

Authors:  Sabrina R Schulz; Siegfried Blechert
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  Construction of asymmetric fluorinated carbon centers.

Authors:  G K Surya Prakash; Petr Beier
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-27       Impact factor: 15.336

10.  Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst.

Authors:  Ryoichi Kuwano; Kei-Ichi Uchida; Yoshihiko Ito
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005

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  63 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

2.  A catalytic, asymmetric formal synthesis of (+)-hamigeran B.

Authors:  Herschel Mukherjee; Nolan T McDougal; Scott C Virgil; Brian M Stoltz
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

Review 3.  Enantioselective protonation.

Authors:  Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

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.  Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork-Danheiser approach: preparation of mono-, bi-, and tricyclic systems.

Authors:  Nathan B Bennett; Allen Y Hong; Andrew M Harned; Brian M Stoltz
Journal:  Org Biomol Chem       Date:  2011-10-19       Impact factor: 3.876

6.  Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine.

Authors:  Arun K Ghosh; Joshua R Born; Luke A Kassekert
Journal:  J Org Chem       Date:  2019-04-02       Impact factor: 4.354

7.  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

8.  Total Synthesis of the Norhasubanan Alkaloid Stephadiamine.

Authors:  Nina Hartrampf; Nils Winter; Gabriele Pupo; Brian M Stoltz; Dirk Trauner
Journal:  J Am Chem Soc       Date:  2018-07-09       Impact factor: 15.419

9.  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

10.  Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

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