Literature DB >> 27224285

Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides.

Xiang-Zhi Zhang1, Yu-Hua Deng2, Xu Yan1, Ke-Yin Yu1, Fang-Xin Wang1, Xiao-Yan Ma1, Chun-An Fan1,3.   

Abstract

A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of para-quinone methides and glycine derivatives is described. This protocol also provides an alternative route to the synthetically interesting functionalized chiral tetrahydroisoquinoline and its analogues.

Entities:  

Year:  2016        PMID: 27224285     DOI: 10.1021/acs.joc.6b00390

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides.

Authors:  Andreas Eitzinger; Michael Winter; Johannes Schörgenhumer; Mario Waser
Journal:  Chem Commun (Camb)       Date:  2019-12-12       Impact factor: 6.222

2.  Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.

Authors:  Katharina Zielke; Mario Waser
Journal:  Org Lett       Date:  2018-01-19       Impact factor: 6.005

3.  Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides.

Authors:  Lukas Roiser; Mario Waser
Journal:  Org Lett       Date:  2017-04-20       Impact factor: 6.005

4.  CF3-Containing para-Quinone Methides for Organic Synthesis.

Authors:  Michael Winter; Roman Schütz; Andreas Eitzinger; Armin R Ofial; Mario Waser
Journal:  European J Org Chem       Date:  2020-03-06

5.  Directed C(sp3)-H arylation of tryptophan: transformation of the directing group into an activated amide.

Authors:  Lennart Nicke; Philip Horx; Klaus Harms; Armin Geyer
Journal:  Chem Sci       Date:  2019-08-08       Impact factor: 9.825

6.  One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides.

Authors:  Junwei Wang; Xiang Pan; Quanjin Rong; Lei Zhao; Lin Zhao; Weichen Dai; Kun Zhao; Lihong Hu
Journal:  RSC Adv       Date:  2020-09-10       Impact factor: 4.036

7.  Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds.

Authors:  Xin Li; Songtao He; Qiuling Song
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

  7 in total

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