Literature DB >> 22052475

Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

Helen K Scott1, Varinder K Aggarwal.   

Abstract

Organoboron compounds are useful in asymmetric synthesis. We have developed an efficient methodology for the highly enantioselective synthesis of tertiary boronic esters from the corresponding secondary benzylic alcohols. Further stereospecific transformations of the boronic ester moiety are described including the preparation of tertiary alcohols, C-tertiary amines and tertiary arylalkanes. Several homologations of tertiary boronic esters have also been developed for the construction of quaternary stereocentres.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2011        PMID: 22052475     DOI: 10.1002/chem.201102581

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  32 in total

1.  Nickel-catalyzed coupling reactions of alkyl electrophiles, including unactivated tertiary halides, to generate carbon-boron bonds.

Authors:  Alexander S Dudnik; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-06-06       Impact factor: 15.419

2.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

3.  Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

Authors:  Daria Kurandina; Mónica Rivas; Maxim Radzhabov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2018-01-05       Impact factor: 6.005

4.  Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.

Authors:  Jesse A Myhill; Liang Zhang; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-29       Impact factor: 15.336

5.  Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy.

Authors:  Ramesh Rasappan; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-07-27       Impact factor: 24.427

6.  Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors:  Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal:  Org Lett       Date:  2019-06-14       Impact factor: 6.005

7.  Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

Authors:  Zhonglin Tao; Kevin A Robb; Jesse L Panger; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-11-09       Impact factor: 15.419

8.  γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors:  Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2012-12-28       Impact factor: 6.222

9.  Forming all-carbon quaternary stereogenic centres in acyclic systems from alkynes.

Authors:  Yury Minko; Morgane Pasco; Lukas Lercher; Mark Botoshansky; Ilan Marek
Journal:  Nature       Date:  2012-10-25       Impact factor: 49.962

10.  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

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