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Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

Affiliation
Institute for Organic Chemistry and Macromolecular Chemistry Friedrich Schiller University Jena Humboldtstrasse 10 07743 Jena Germany
Nosovska, Olena;
GND
1276149425
Affiliation
Institute of Inorganic and Analytical Chemistry Friedrich Schiller University Jena Humboldtstrasse 8 07743 Jena Germany
Liebing, Phil;
GND
1175585130
ORCID
0000-0001-6199-0632
Affiliation
Institute for Organic Chemistry and Macromolecular Chemistry Friedrich Schiller University Jena Humboldtstrasse 10 07743 Jena Germany
Vilotijevic, Ivan

Trifluoro‐ and trichloroacetamides serving as pronucleophiles undergo enantioselective Lewis base catalyzed N ‐allylation with Morita‐Baylis‐Hillman carbonates to produce enantioenriched β‐amino acid derivatives. The reactions proceed as a kinetic resolution to give the allylation products and the remaining carbonates in good yields and high enantioselectivity. The obtained products are amenable to diastereoselective derivatization to produce a library of spiro‐isoxazoline lactams.

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Published in:
Chemistry – A European Journal
Vol. 30, No. 14 (08.03.2024)Art.-No.:e202304014, p. 1-7
Volume:
30
No.:
14
Date Issued:
08.03.2024
URN:
urn:nbn:de:gbv:27-dbt-20240418-135447-007
DOI:
10.1002/chem.202304014
Language:
English
Type of Resource:
Text
Extent:
7 Seiten
Keywords:
  1. β-amino acid
    Typ
    Schlagwort
  1. Lewis base catalysis
    Typ
    Schlagwort
  1. Morita Baylis Hillman adducts
    Typ
    Schlagwort
  1. enantioselective synthesis
    Typ
    Schlagwort
  1. spiro compounds
    Typ
    Schlagwort
DDC subject of DNB:
540 Chemistry & allied sciences
Hosting institution:
Friedrich-Schiller-Universität Jena, Chemisch-Geowissenschaftliche Fakultät
note:
Zweitveröffentlichung

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