Literature DB >> 30505454

Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

Vito Capaccio1,2, Katharina Zielke1, Andreas Eitzinger1, Antonio Massa2, Laura Palombi2, Kirill Faust3, Mario Waser1.   

Abstract

A novel high yielding, enantio- and diastereoselective protocol for the synthesis of α-allylated highly functionalised β-amino acid derivatives by adding isoxazolidin-5-ones to MBH carbonates under asymmetric phase-transfer catalysis has been developed.

Entities:  

Year:  2018        PMID： 30505454      PMCID： PMC6261335          DOI： 10.1039/C8QO01057A

Source DB:  PubMed          Journal:  Org Chem Front        ISSN： 2052-4110            Impact factor:   5.281


  29 in total

1.  A new generation of chiral phase-transfer catalysts.

Authors:  Shiho Kaneko; Yusuke Kumatabara; Seiji Shirakawa
Journal:  Org Biomol Chem       Date:  2016-01-12       Impact factor: 3.876

Review 2.  Recent development and application of chiral phase-transfer catalysts.

Authors:  Takuya Hashimoto; Keiji Maruoka
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

3.  Recent developments in asymmetric phase-transfer reactions.

Authors:  Seiji Shirakawa; Keiji Maruoka
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-28       Impact factor: 15.336

4.  Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2 -Amino Acids.

Authors:  Marllon Nascimento de Oliveira; Stellios Arseniyadis; Janine Cossy
Journal:  Chemistry       Date:  2018-03-13       Impact factor: 5.236

5.  Pd/Cu dual catalysis: highly enantioselective access to α-substituted α-amino acids and α-amino amides.

Authors:  Xiaohong Huo; Jingke Fu; Xiaobo He; Jianzhong Chen; Fang Xie; Wanbin Zhang
Journal:  Chem Commun (Camb)       Date:  2018-01-16       Impact factor: 6.222

6.  Exploiting β-Amino Acid Enolates in Direct Catalytic Diastereo- and Enantioselective C-C Bond-Forming Reactions.

Authors:  Jin-Sheng Yu; Hidetoshi Noda; Masakatsu Shibasaki
Journal:  Chemistry       Date:  2018-10-08       Impact factor: 5.236

7.  Phase-Transfer and Ion-Pairing Catalysis of Pentanidiums and Bisguanidiniums.

Authors:  Lili Zong; Choon-Hong Tan
Journal:  Acc Chem Res       Date:  2017-04-05       Impact factor: 22.384

8.  The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

Authors:  Martin J O'Donnell
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  Highly enantioselective Cu-catalyzed conjugate addition-elimination of activated allylic acetates with glycine derivatives.

Authors:  Chun-Gen Chen; Xue-Long Hou; Lin Pu
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

10.  Catalyst-controlled switch of regioselectivity in the asymmetric allylic alkylation of oxazolones with MBHCs.

Authors:  Gongming Zhu; Junxian Yang; Guangjun Bao; Ming Zhang; Jing Li; Yiping Li; Wangsheng Sun; Liang Hong; Rui Wang
Journal:  Chem Commun (Camb)       Date:  2016-06-14       Impact factor: 6.222
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  5 in total

1.  Enantioselective catalytic synthesis of α-aryl-α-SCF3-β2,2-amino acids.

Authors:  Andreas Eitzinger; Jean-François Brière; Dominique Cahard; Mario Waser
Journal:  Org Biomol Chem       Date:  2020-01-22       Impact factor: 3.876

2.  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

3.  Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Authors:  Michael Winter; Kirill Faust; Markus Himmelsbach; Mario Waser
Journal:  Org Biomol Chem       Date:  2019-06-12       Impact factor: 3.876

4.  Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives.

Authors:  Victoria Haider; Paul Zebrowski; Jessica Michalke; Uwe Monkowius; Mario Waser
Journal:  Org Biomol Chem       Date:  2022-01-26       Impact factor: 3.890

5.  Enantioselective Catalytic Synthesis of α-Halogenated α-Aryl-β2,2-amino Acid Derivatives.

Authors:  Paul Zebrowski; Isabella Eder; Andreas Eitzinger; Sharath Chandra Mallojjala; Mario Waser
Journal:  ACS Org Inorg Au       Date:  2021-09-24
  5 in total

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