Literature DB >> 29436035

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

Marllon Nascimento de Oliveira1, Stellios Arseniyadis1,2, Janine Cossy1.   

Abstract

We report here an unprecedented and highly enantioselective palladium-catalyzed allylic alkylation applied to 4-substituted isoxazolidin-5-ones. Ultimately, the process provides a straightforward access to β2,2 -amino acids bearing an all-carbon quaternary stereogenic center in great yields and a high degree of enantioselectivity.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic alkylation; asymmetric catalysis; beta-lactams; beta2,2-amino acids; isoxazolidinones; palladium

Mesh:

Substances:

Year:  2018        PMID: 29436035     DOI: 10.1002/chem.201800641

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  Enantioselective catalytic synthesis of α-aryl-α-SCF32,2-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.  Fuel-driven macromolecular coacervation in complex coacervate core micelles.

Authors:  Reece W Lewis; Benjamin Klemm; Mariano Macchione; Rienk Eelkema
Journal:  Chem Sci       Date:  2022-03-31       Impact factor: 9.969

3.  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

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

Authors:  Vito Capaccio; Katharina Zielke; Andreas Eitzinger; Antonio Massa; Laura Palombi; Kirill Faust; Mario Waser
Journal:  Org Chem Front       Date:  2018-10-12       Impact factor: 5.281

6.  On the hydrolysis of diethyl 2-(perfluorophenyl)malonate.

Authors:  Ilya V Taydakov; Mikhail A Kiskin
Journal:  Beilstein J Org Chem       Date:  2020-07-28       Impact factor: 2.883

7.  A modular and divergent approach to spirocyclic pyrrolidines.

Authors:  Benjamin D A Shennan; Peter W Smith; Yusuke Ogura; Darren J Dixon
Journal:  Chem Sci       Date:  2020-08-07       Impact factor: 9.825

  7 in total

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