6533b82cfe1ef96bd128f546
RESEARCH PRODUCT
Role of the gem-Difluoro Moiety in the Tandem Ring-Closing Metathesis−Olefin Isomerization: Regioselective Preparation of Unsaturated Lactams
Jose Luis AcenaCarlos Del PozoSantos FusteroDiego JimenezMaría Sánchez-rosellóJuan F. Sanz-cerverasubject
Olefin fiberOrganic ChemistryRegioselectivityGeneral MedicineMetathesisCombinatorial chemistrychemistry.chemical_compoundRing-closing metathesischemistryCascade reactionSalt metathesis reactionLactamOrganic chemistryMoietyIsomerizationdescription
Careful selection of the metathesis catalyst, solvent, and reaction conditions allows for the efficient and regioselective synthesis of isomeric fluorinated and nonfluorinated lactam derivatives II and III from precursor amides I through a ring-closing metathesis (RCM) reaction or a tandem RCM-isomerization protocol, respectively. The presence of the gem-difluoro moiety in the starting materials exerts a pivotal effect by directing the isomerization step, making the overall tandem transformation a regioselective process. The scope, limitations, and synthetic usefulness of this protocol are also discussed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-08-22 | The Journal of Organic Chemistry |