Literature DB >> 33041522

Stereoselective α-Tertiary Alkylation of N-(Arylacetyl)oxazolidinones.

Eunjae Shim1, Armen Zakarian1.   

Abstract

A method has been developed for the α-tertiary alkylation of zirconium enolates of N-(arylacetyl)oxazolidinones. This reaction directly installs an all-carbon quaternary center vicinal to a benzylic tertiary carbon in a highly diastereoselective manner.

Entities:  

Keywords:  alkylation; asymmetric synthesis; chiral auxiliary; oxazolidinones; quaternary carbon; zirconium enolates

Year:  2020        PMID： 33041522      PMCID： PMC7544157          DOI： 10.1055/s-0039-1690793

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  10 in total

Review 1.  Direct construction of vicinal all-carbon quaternary stereocenters in natural product synthesis.

Authors:  Rong Long; Jun Huang; Jianxian Gong; Zhen Yang
Journal:  Nat Prod Rep       Date:  2015-09-03       Impact factor: 13.423

2.  Unconventional biradical character of titanium enolates.

Authors:  I de P R Moreira; J M Bofill; J M Anglada; J G Solsona; J Nebot; P Romea; F Urpí
Journal:  J Am Chem Soc       Date:  2008-02-21       Impact factor: 15.419

3.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

4.  Construction of Quaternary Stereogenic Centers in the Total Synthesis of Natural Products.

Authors:  Evgeny V Prusov
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-14       Impact factor: 15.336

5.  Stereoselective α-fluorination of N-acyloxazolidinones at room temperature within 1 h.

Authors:  Joseph Alvarado; Aaron T Herrmann; Armen Zakarian
Journal:  J Org Chem       Date:  2014-06-20       Impact factor: 4.354

6.  Stereoselective aminoxylation of biradical titanium enolates with TEMPO.

Authors:  Alejandro Gómez-Palomino; Miquel Pellicena; Juan Manuel Romo; Ricard Solà; Pedro Romea; Fèlix Urpí; Mercè Font-Bardia
Journal:  Chemistry       Date:  2014-07-07       Impact factor: 5.236

Review 7.  SuperQuat chiral auxiliaries: design, synthesis, and utility.

Authors:  Stephen G Davies; Ai M Fletcher; Paul M Roberts; James E Thomson
Journal:  Org Biomol Chem       Date:  2019-02-06       Impact factor: 3.876

8.  A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates.

Authors:  Aaron T Herrmann; Lindsay L Smith; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2012-04-12       Impact factor: 15.419

9.  Valence tautomerism in titanium enolates: catalytic radical haloalkylation and application in the total synthesis of neodysidenin.

Authors:  Stéphane Beaumont; Elizabeth A Ilardi; Lucas R Monroe; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

10.  Asymmetric radical addition of TEMPO to titanium enolates.

Authors:  Phillip J Mabe; Armen Zakarian
Journal:  Org Lett       Date:  2013-12-31       Impact factor: 6.005
  10 in total

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