Literature DB >> 31934766

Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.

Jacob C Green1, Joseph M Zanghi1, Simon J Meek1.   

Abstract

A Cu-catalyzed method for the efficient enantio- and diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable γ,γ-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.

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Year:  2020        PMID： 31934766      PMCID： PMC7180160          DOI： 10.1021/jacs.9b11529

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  49 in total

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Journal:  J Am Chem Soc       Date:  2016-10-20       Impact factor: 15.419

6.  Catalytic enantioselective construction of quaternary stereocenters: assembly of key building blocks for the synthesis of biologically active molecules.

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7.  Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.

Authors:  Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

8.  Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres.

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  5 in total

1.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

2.  Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors:  Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

3.  α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Authors:  Chenlong Zhang; Weipeng Hu; James P Morken
Journal:  ACS Catal       Date:  2021-08-12       Impact factor: 13.700

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Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

5.  Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.

Authors:  Toolika Agrawal; Robert T Martin; Stephen Collins; Zachary Wilhelm; Mytia D Edwards; Osvaldo Gutierrez; Joshua D Sieber
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  5 in total

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