Literature DB >> 18303896

Homogeneous pd-catalyzed enantioselective decarboxylative protonation.

Smaranda C Marinescu1, Toyoki Nishimata, Justin T Mohr, Brian M Stoltz.   

Abstract

General homogeneous conditions for the palladium-catalyzed synthesis of carbonyl compounds with tertiary carbon stereocenters at the alpha-position are reported. The highly reactive catalyst tolerates a variety of substrate substitution and functionality, and generates enantioenriched cyclic ketones from racemic allyl beta-ketoester starting materials.

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Year:  2008        PMID： 18303896      PMCID： PMC2966305          DOI： 10.1021/ol702821j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  21 in total

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2.  The enantioselective Tsuji allylation.

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

3.  Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters.

Authors:  Carsten Schaefer; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

4.  Enantioselective protonation of silyl enolates catalyzed by a BinapAgF complex.

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Journal:  Angew Chem Int Ed Engl       Date:  2005-02-25       Impact factor: 15.336

5.  Organocatalytic enantioselective protonation of silyl enolates mediated by cinchona alkaloids and a latent source of HF.

Authors:  Thomas Poisson; Vincent Dalla; Francis Marsais; Georges Dupas; Sylvain Oudeyer; Vincent Levacher
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of alpha-chloroesters.

Authors:  Nathan T Reynolds; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

7.  Enantioselective partial reduction of 2,5-disubstituted pyrroles via a chiral protonation approach.

Authors:  Timothy J Donohoe; Graeme C Freestone; Catherine E Headley; Caroline L Rigby; Rick P C Cousins; Gurdip Bhalay
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

8.  Rhodium-catalyzed conjugate addition-enantioselective protonation: the synthesis of alpha,alpha'-dibenzyl esters.

Authors:  Christopher G Frost; Stephen D Penrose; Kim Lambshead; Paul R Raithby; John E Warren; Robert Gleave
Journal:  Org Lett       Date:  2007-04-28       Impact factor: 6.005

9.  A facile and modular synthesis of phosphinooxazoline ligands.

Authors:  Kousuke Tani; Douglas C Behenna; Ryan M McFadden; Brian M Stoltz
Journal:  Org Lett       Date:  2007-05-31       Impact factor: 6.005

10.  Amine-salt-controlled, catalytic asymmetric conjugate addition of various amines and asymmetric protonation.

Authors:  Yoshitaka Hamashima; Hidenori Somei; Yuta Shimura; Toshihiro Tamura; Mikiko Sodeoka
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
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  16 in total

Review 1.  Enantioselective protonation.

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

2.  Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors:  Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2010-10-20       Impact factor: 2.415

3.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

4.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

5.  Palladium-Catalyzed Asymmetric Alkylation in the Synthesis of Cyclopentanoid and Cycloheptanoid Core Structures Bearing All-Carbon Quaternary Stereocenters.

Authors:  Allen Y Hong; Nathan B Bennett; Michael R Krout; Thomas Jensen; Andrew M Harned; Brian M Stoltz
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

6.  PREPARATION OF (S)-2-Allyl-2-methylcyclohexanone (Cyclohexanone, 2-methyl-2-(2-propen-1-yl)-, (2S)-).

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Organic Synth       Date:  2009

7.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

8.  PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-).

Authors:  Michael R Krout; Justin T Mohr; Brian M Stoltz
Journal:  Organic Synth       Date:  2009-01-01

9.  Synthesis and Exploration of Electronically Modified (R)-5,5-Dimethyl-(p-CF3)3-i-PrPHOX in Palladium-Catalyzed Enantio- and Diastereoselective Allylic Alkylation: A Practical Alternative to (R)-(p-CF3)3-t-BuPHOX.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2015-08-05       Impact factor: 2.415

10.  Enantioselective total synthesis of (+)-cassiol.

Authors:  Krastina V Petrova; Justin T Mohr; Brian M Stoltz
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005
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