Literature DB >> 19185046

Asymmetric hydroboration of 1,1-disubstituted alkenes.

Stephen P Thomas1, Varinder K Aggarwal.   

Abstract

A breakthrough in the asymmetric hydroboration of notoriously difficult 1,1-disubstituted alkenes using a new family of highly effective hydroboration reagents is described (see scheme). The intermediate boranes can be oxidized to alcohols or used in Suzuki-Miyaura cross-coupling reactions.

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Year:  2009        PMID： 19185046     DOI： 10.1002/anie.200805604

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre.

Authors:  Jaehee Lee; Suttipol Radomkit; Sebastian Torker; Juan Del Pozo; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

2.  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

3.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

4.  From synthesis to function via iterative assembly of N-methyliminodiacetic acid boronate building blocks.

Authors:  Junqi Li; Anthony S Grillo; Martin D Burke
Journal:  Acc Chem Res       Date:  2015-07-22       Impact factor: 22.384

5.  Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Authors:  Mingkai Zhang; Peilin Xu; Alex J Vendola; Christophe Allais; Anne-Marie Dechert Schmitt; Robert A Singer; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-08       Impact factor: 16.823

6.  Quantum-mechanical study of 10-R-9-borabicyclo[3.3.2]decane alkene hydroboration.

Authors:  Daniel H Ess; Jeremy Kister; Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

Review 7.  Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.

Authors:  Michael T Pirnot; Yi-Ming Wang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

8.  Pinene-derived iminodiacetic acid (PIDA): a powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp3) boronate building blocks.

Authors:  Junqi Li; Martin D Burke
Journal:  J Am Chem Soc       Date:  2011-08-10       Impact factor: 15.419

9.  Enantioselective CuH-catalyzed anti-Markovnikov hydroamination of 1,1-disubstituted alkenes.

Authors:  Shaolin Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-10-29       Impact factor: 15.419

10.  Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes.

Authors:  James R Smith; Beatrice S L Collins; Matthew J Hesse; Mark A Graham; Eddie L Myers; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-06-30       Impact factor: 15.419
  10 in total

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