6533b82dfe1ef96bd129141d
RESEARCH PRODUCT
Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis.
Santos FusteroCarlos Del PozoBegona FernandezAnd Amparo AsensioCarmen Ramírez De ArellanoJuan F. Sanz-cerveraMaría Sánchez-rosellóAna BartolomeJosé Luis Aceñasubject
chemistry.chemical_classificationStereochemistryOrganic ChemistryEnantioselective synthesisFluorineMetathesisBiochemistryCatalysisAmino acidchemistryCyclizationOrganic chemistryPhysical and Theoretical ChemistryAmino AcidsBeta (finance)description
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-09-22 | Organic letters |