6533b828fe1ef96bd1287955
RESEARCH PRODUCT
Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α- chloroimines
Melinda NonnGert CallebautKarl W. TörnroosSven MangelinckxReijo SillanpääFilip ColpaertLoránd KissFerenc FülöpNorbert De Kimpesubject
Models MolecularThreonineState modelStereochemistryOrganic ChemistryChlorine atomEnantioselective synthesischemistry.chemical_elementEstersStereoisomerismCrystallography X-RayBiochemistryOxygenMannich BaseschemistryHydrocarbons ChlorinatedSide chainLithiumStereoselectivityChelationIminesPhysical and Theoretical Chemistryta116description
Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-α-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new γ-chloro-α-hydroxy-β-amino esters (dr > 99:1). The α-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the lithium ion of the incoming E-enolate in the transition state model. These novel chloroisothreonine derivatives proved to be excellent building blocks in asymmetric synthesis of novel syn-β,γ-aziridino-α-hydroxy esters and biologically relevant trans-oxazolidinone carboxylic esters.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-04-18 | Organic and Biomolecular Chemistry |