6533b838fe1ef96bd12a4891
RESEARCH PRODUCT
Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates
José SeguraLuis R. DomingoSalvador GilMargarita Parrasubject
diastereoselectivity.Carboxylic acidCarboxylic AcidsPharmaceutical ScienceEpoxideMedicinal chemistryAnalytical Chemistrylcsh:QD241-441chemistry.chemical_compoundLactoneslcsh:Organic chemistryNucleophileStyrene oxideDrug DiscoveryOrganic chemistryPhysical and Theoretical Chemistrylithium chloridechemistry.chemical_classificationNucleophilic additionCommunicationOrganic ChemistryDiastereomerRegioselectivitydiastereoselectivitynucleophilic additionchemistryChemistry (miscellaneous)regioselectivityMolecular MedicineEpoxy CompoundsAmine gas treatingdescription
Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-06-01 | Molecules |