Literature DB >> 22175222

Asymmetric synthesis of trisubstituted allenes: copper-catalyzed alkylation and arylation of propargylic phosphates.

Mycah R Uehling1, Samuel T Marionni, Gojko Lalic.   

Abstract

Asymmetric synthesis of trisubstituted allenes is accomplished by copper-catalyzed alkylation and arylation of propargylic phosphates using organoboron nucleophiles. Excellent chirality transfer and regioselectivity, together with good functional group compatibility, were observed in reactions with both alkyl boranes and arylboronic esters.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 22175222     DOI： 10.1021/ol2031119

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


  9 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

Authors:  Yao Jiang; Abdallah B Diagne; Regan J Thomson; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2017-01-25       Impact factor: 15.419

3.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

4.  An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates.

Authors:  Michael L Conner; M Kevin Brown
Journal:  Tetrahedron       Date:  2016-02-18       Impact factor: 2.457

5.  Iron-catalyzed Cross-Coupling of Propargyl Carboxylates and Grignard Reagents: Synthesis of Substituted Allenes.

Authors:  Simon N Kessler; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

6.  Re-Orienting Coupling of Organocuprates with Propargyl Electrophiles from SN2' to SN2 with Stereocontrol.

Authors:  Barry M Trost; Laurent Debien
Journal:  Chem Sci       Date:  2016-05-10       Impact factor: 9.825

7.  Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.

Authors:  Jian-Siang Poh; Szabolcs Makai; Timo von Keutz; Duc N Tran; Claudio Battilocchio; Patrick Pasau; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-11       Impact factor: 15.336

8.  Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes.

Authors:  Zheng-Li Liu; Chao Yang; Qi-Yan Xue; Meng Zhao; Cui-Cui Shan; Yun-He Xu; Teck-Peng Loh
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-04       Impact factor: 15.336

9.  Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.

Authors:  Roly J Armstrong; Meganathan Nandakumar; Rafael M P Dias; Adam Noble; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-30       Impact factor: 15.336
  9 in total

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