6533b7dbfe1ef96bd1270b2c
RESEARCH PRODUCT
Diastereoselectivity of the Addition of Propargylic Magnesium Reagents to Fluorinated Aromatic Sulfinyl Imines.
Mercedes Medio-simónSantos FusteroJorge EscorihuelaAlberto Llobatsubject
010405 organic chemistryMagnesiumfungiOrganic Chemistryfood and beverageschemistry.chemical_element010402 general chemistry01 natural sciencesBiochemistry0104 chemical scienceschemistry.chemical_compoundchemistryBromideReagentOrganic chemistryPhysical and Theoretical Chemistrydescription
The addition of propargylmagnesium bromide to fluorinated aromatic sulfinyl imines gave homopropargyl amines with total regio- and diastereoselection. Complete reversal of diastereoselectivity can be achieved in some cases using coordinating (THF) or noncoordinating (DCM) solvents. Substituted propargylic magnesium reagents have been also tested toward fluorinated aryl sulfinyl imines affording chiral homoallenyl amines with good yields and selectivity control. DFT calculations helped to rationalize the origin of the experimental regio- and diastereoselectivities observed in each case.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-04-22 | Organic letters |