6533b7d4fe1ef96bd1261cb6
RESEARCH PRODUCT
Enzymatic esterification of bicyclic meso-diols derived from 1,4-bis(hydroxymethyl)furan. An enantioselective Diels–Alder reaction equivalent
Cecilia AndreuTeresa VareaJuan-pablo VillarroyaJuan Server-carrióMercedes Medio-simónAmadeo Garcı́a-gastaldisubject
Dimethyl acetylenedicarboxylateBicyclic moleculeChemistryOrganic ChemistryEnantioselective synthesisMedicinal chemistryCatalysisAdductInorganic Chemistrychemistry.chemical_compoundFuranHydroxymethylPhysical and Theoretical ChemistryDerivative (chemistry)Diels–Alder reactiondescription
Abstract meso -Diols derived from the Diels–Alder adduct 1,4-bis(hydroxymethyl)furan/dimethyl acetylenedicarboxylate can be enantioselectively monoacetylated under CRL or PSL catalysis with very good yields and moderate to excellent ees. (+)-Monoacetates are always preferentially formed in the reactions catalyzed by CRL, and their (−)-enantiomers are the main products in the acetylations under PSL catalysis. Absolute configurations have been determined by X-ray analysis of a single crystal of an ( R )-α-methoxyphenylacetyl derivative.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-09-01 | Tetrahedron: Asymmetry |