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RESEARCH PRODUCT
Asymmetric Synthesis of New β,β-Difluorinated Cyclic Quaternary α-Amino Acid Derivatives
Carlos Del PozoCarmen Ramírez De ArellanoVanessa RodrigoJuan F. Sanz-cerveraSantos FusteroAnd Antonio SimónMaría Sánchez-rosellósubject
Chiral auxiliaryStereochemistryOrganic ChemistryEnantioselective synthesisEtherBiochemistryStereocenterchemistry.chemical_compoundchemistrySalt metathesis reactionStereoselectivityPhysical and Theoretical ChemistryEnantiomerSelectivitydescription
The synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives 1 in which a ring-closing metathesis reaction (RCM) constitutes the key step is described. The approach employs imidoyl chlorides 3 as fluorinated building blocks, and the overall process involves the stereoselective creation of a quaternary stereocenter. Complete selectivity was achieved when (R)-phenylglycinol methyl ether was used as chiral auxiliary, allowing for the preparation of new six-membered cyclic fluorinated alpha-amino acids as single enantiomers.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-08-01 | Organic Letters |