Literature DB >> 20597474

Synthesis of alpha-arylated allylsilanes through palladium-catalyzed gamma-selective allyl-aryl coupling.

Dong Li1, Tatsunori Tanaka, Hirohisa Ohmiya, Masaya Sawamura.   

Abstract

A palladium-catalyzed gamma-selective allyl-aryl coupling between gamma-silylated allylic esters and arylboronic acids produced alpha-arylated allylsilanes with E-alkene geometry. The reaction tolerated various functional groups in both the arylboronic acids and the allylic esters and afforded functionalized allylsilanes. The reaction of optically active allylic esters took place with excellent alpha-to-gamma chirality transfer with syn stereochemistry to give chiral allylsilanes.

Entities:  

Year:  2010        PMID： 20597474     DOI： 10.1021/ol101114r

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


  6 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.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

3.  Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Authors:  Harathi D Srinivas; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005

4.  Enantioselective Nickel-Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization.

Authors:  Connor Yap; Gabriel M J Lenagh-Snow; Somnath Narayan Karad; William Lewis; Louis J Diorazio; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-12       Impact factor: 15.336

5.  Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles.

Authors:  Alan H Cherney; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2014-10-01       Impact factor: 15.419

6.  Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles.

Authors:  Cristina García-Ruiz; Jack L-Y Chen; Christopher Sandford; Kathryn Feeney; Paula Lorenzo; Guillaume Berionni; Herbert Mayr; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-10-20       Impact factor: 15.419
  6 in total

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