6533b870fe1ef96bd12d0393
RESEARCH PRODUCT
First Highly Diastereoselective Synthesis of syn α-Methyl β-Fluoroalkyl β-Amino Esters
Antonio Hidalgo NavarroSantos FusteroMarta Garcia De La TorreAnd Carmen Ramírez De ArellanoBelén PinaAntonio Simónsubject
chemistryAmino estersReducing agentOrganic ChemistryChemical reductionchemistry.chemical_elementLithiumPhysical and Theoretical ChemistryBiochemistryMedicinal chemistryRedoxdescription
A new two-step approach for the diastereoselective synthesis of the syn α-methyl β-fluoroalkyl β-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated β-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with ZnI2/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1999-09-09 | Organic Letters |