Literature DB >> 19885455

Expanding the scope of transformations of organoboron species: carbon-carbon bond formation with retention of configuration.

Cathleen M Crudden1, Ben W Glasspoole, Christopher J Lata.   

Abstract

The use of boron chemistry for the synthesis of enantiomerically enriched organic compounds is described. Key advances towards the preparation of organoboranes with control of stereochemistry are supplemented by a discussion of the use of these chiral organoboranes in carbon-carbon bond forming reactions. Particular emphasis is given to advances in the Suzuki-Miyaura coupling of chiral secondary organoboranes and homologation reactions. Both of these reactions convert the initially generated B-C bond into a C-C bond and thus lead to a significant increase in complexity.

Entities:  

Year:  2009        PMID: 19885455     DOI: 10.1039/b911537d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  16 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.  Palladium-catalyzed borylation of primary alkyl bromides.

Authors:  Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal:  J Org Chem       Date:  2012-07-23       Impact factor: 4.354

3.  Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Authors:  Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-08       Impact factor: 15.419

4.  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

5.  Remarkable levels of enantioswitching in catalytic asymmetric hydroboration.

Authors:  Sean M Smith; James M Takacs
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

6.  Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Timothy J Barker
Journal:  Organometallics       Date:  2018-04-27       Impact factor: 3.876

7.  Beyond benzyl grignards: facile generation of benzyl carbanions from styrenes.

Authors:  R David Grigg; Jared W Rigoli; Ryan Van Hoveln; Samuel Neale; Jennifer M Schomaker
Journal:  Chemistry       Date:  2012-06-20       Impact factor: 5.236

8.  Diastereoselective aziridination of 2-B(pin)-substituted allylic alcohols: an efficient approach to novel organoboron compounds.

Authors:  Jorge Hernández-Toribio; Mahmud M Hussain; Kevin Cheng; Patrick J Carroll; Patrick J Walsh
Journal:  Org Lett       Date:  2011-10-25       Impact factor: 6.005

9.  Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes.

Authors:  Sean M Smith; James M Takacs
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

10.  Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration.

Authors:  R David Grigg; Ryan Van Hoveln; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-09-19       Impact factor: 15.419

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