6533b851fe1ef96bd12a967c
RESEARCH PRODUCT
A New Tandem Cross Metathesis-Intramolecular Aza-Michael Reaction for the Synthesis of α,α-Difluorinated Lactams
Claribel BáezSantos FusteroAmparo AsensioCarlos Del PozoMaría Sánchez-rosellóJavier Mirósubject
chemistry.chemical_compoundNucleophileTandemchemistryIntramolecular forceAmideOrganic ChemistryEnantioselective synthesisMichael reactionMetathesisCombinatorial chemistryCatalysisCatalysisdescription
A new tandem cross metathesis–intramolecular aza-Michael reaction in which an α,α-difluorinated amide serves as a source of nucleophilic nitrogen is described. This process gives rise to a new family of fluorinated γ- and δ-lactams. The tandem protocol is catalyzed by the Hoveyda–Grubbs second-generation ruthenium catalyst with titanium(IV) tetraisopropoxide as a co-catalyst and it is highly efficient when conjugated ketones are used as the Michael acceptors. With conjugated esters, however, it is necessary to perform a step-by-step procedure in which the cyclization event is activated by the addition of a base. An asymmetric version of the process is also evaluated.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-04-27 | Synthesis |