Literature DB >> 20856962

Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate.

Qiao-Qiao Min1, Chun-Yang He, Haibing Zhou, Xingang Zhang.   

Abstract

An efficient method for highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids was developed via indium mediated allylation of (R)-phenylglycinol methyl ether based imines of trifluoropyruvate in good yields with high diastereoselectivities at room temperature; to illustrate the application of this method in organic synthesis, 2-allyl-2-(trifluoromethyl) aziridine was prepared in an efficient manner.

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Year:  2010        PMID: 20856962     DOI: 10.1039/c0cc02408b

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


  4 in total

1.  A Broad Substrate Scope of Aza-Friedel-Crafts Alkylation for the Synthesis of Quaternary α-Amino Esters.

Authors:  Guangkuan Zhao; Shyam S Samanta; Jessica Michieletto; Stéphane P Roche
Journal:  Org Lett       Date:  2020-07-10       Impact factor: 6.005

2.  An expeditious route to sterically encumbered nonproteinogenic α-amino acid precursors using allylboronic acids.

Authors:  Samrat Sahu; Ganesh Karan; Lisa Roy; Modhu Sudan Maji
Journal:  Chem Sci       Date:  2022-01-28       Impact factor: 9.825

3.  Pd-Catalyzed Allylation of Imines to Access α-CF3-Substituted α-Amino Acid Derivatives.

Authors:  Michael Winter; Hyunwoo Kim; Mario Waser
Journal:  European J Org Chem       Date:  2019-10-09

4.  Enantioselective Synthesis of α-Trifluoromethyl Amines via Biocatalytic N-H Bond Insertion with Acceptor-Acceptor Carbene Donors.

Authors:  Donggeon Nam; Antonio Tinoco; Zhuofan Shen; Ronald D Adukure; Gopeekrishnan Sreenilayam; Sagar D Khare; Rudi Fasan
Journal:  J Am Chem Soc       Date:  2022-02-02       Impact factor: 15.419

  4 in total

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