Literature DB >> 21076623

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

Nolan T McDougal1, Jan Streuff, Herschel Mukherjee, Scott C Virgil, Brian M Stoltz.   

Abstract

Herein an efficient and direct copper-catalyzed coupling of oxazoline-containing aryl bromides with electron-deficient secondary phosphine oxides is reported. The resulting tertiary phosphine oxides can be reduced to prepare a range of PHOX ligands. The presented strategy is a useful alternative to known methods for constructing PHOX derivatives.

Entities:  

Year:  2010        PMID： 21076623      PMCID： PMC2976555          DOI： 10.1016/j.tetlet.2010.08.039

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  21 in total

1.  Recent developments in the application of oxazoline-containing ligands in asymmetric catalysis.

Authors:  Helen A McManus; Patrick J Guiry
Journal:  Chem Rev       Date:  2004-09       Impact factor: 60.622

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.  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

4.  Rhodium-catalyzed enantioselective desymmetrization of meso-3,5-dimethyl glutaric anhydride: a general strategy to syn-deoxypolypropionate synthons.

Authors:  Matthew J Cook; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2007-07-10       Impact factor: 15.419

5.  The catalytic asymmetric total synthesis of elatol.

Authors:  David E White; Ian C Stewart; Robert H Grubbs; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2007-12-29       Impact factor: 15.419

6.  Proline/pipecolinic acid-promoted copper-catalyzed P-arylation.

Authors:  Cheng Huang; Xu Tang; Hua Fu; Yuyang Jiang; Yufen Zhao
Journal:  J Org Chem       Date:  2006-06-23       Impact factor: 4.354

7.  Intramolecular Enantioselective Palladium-Catalyzed Heck Arylation of Cyclic Enamides.

Authors:  Lena Ripa; Anders Hallberg
Journal:  J Org Chem       Date:  1997-02-07       Impact factor: 4.354

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.  Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides.

Authors:  Dmitri Gelman; Lei Jiang; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005

10.  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
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  14 in total

1.  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

2.  Construction of Tertiary Chiral Centers by Pd-catalyzed Asymmetric Allylic Alkylation of Prochiral Enolate Equivalents.

Authors:  Yusuke Kita; Yoshitaka Numajiri; Noriko Okamoto; Brian M Stoltz
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

3.  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

4.  A FISCHER INDOLIZATION STRATEGY TOWARD THE TOTAL SYNTHESIS OF (-)-GONIOMITINE.

Authors:  Beau P Pritchett; Jun Kikuchi; Yoshitaka Numajiri; Brian M Stoltz
Journal:  Heterocycles       Date:  2017-02-15       Impact factor: 0.831

5.  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

6.  Enantioselective Total Synthesis of Nigelladine A via Late-Stage C-H Oxidation Enabled by an Engineered P450 Enzyme.

Authors:  Steven A Loskot; David K Romney; Frances H Arnold; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-07-24       Impact factor: 15.419

7.  Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

Authors:  Nathan B Bennett; Douglas C Duquette; Jimin Kim; Wen-Bo Liu; Alexander N Marziale; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2013-02-27       Impact factor: 5.236

8.  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

9.  Catalytic enantioselective total synthesis of (+)-eucomic acid.

Authors:  Benzi I Estipona; Beau P Pritchett; Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron       Date:  2016-03-02       Impact factor: 2.457

10.  Development of asymmetric deacylative allylation.

Authors:  Alexander J Grenning; Christie K Van Allen; Tapan Maji; Simon B Lang; Jon A Tunge
Journal:  J Org Chem       Date:  2013-07-01       Impact factor: 4.354
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