Synthesis of Enantiopure Benzyl Homoallylamines by Indium-Mediated Barbier-Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N-Containing Heterocycles

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Publikationens författare: Ari Hietanen, Tiina Saloranta, Sara Rosenberg, Evelina Laitinen, Reko Leino and Liisa T. Kanerva
Förläggare: WILEY-V C H VERLAG GMBH
Publiceringsår: 2010
Tidskrift: European Journal of Organic Chemistry
Tidskriftsakronym: EUR J ORG CHEM
Volym: 2010
Nummer: 5
Artikelns första sida, sidnummer: 909
Artikelns sista sida, sidnummer: 919
Antal sidor: 11
ISSN: 1434-193X


Abstrakt

Barbier-type indium-mediated allylations of different N,N(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding (S)-amines and (R)-amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide could be converted into unsaturated lactams in a straightforward manner by utilizing ring-closing metathesis. Furthermore, the enantiopure (S)-1-phenylbut-3-enylamine was converted into the corresponding diallylamine, which was subjected to ring-closing metathesis to yield a substituted dehydropiperidine mimicking a number of natural products.


Nyckelord

Allylation, Amines, Enzyme catalysis, Kinetic resolution, Ring-closing metathesis

Senast uppdaterad 2020-24-02 vid 03:41