Diastereoselectivity of the Addition of Propargylic Magnesium Reagents to Fluorinated Aromatic Sulfinyl Imines | Zendy

Alberto Llobat | Zendy; Jorge Escorihuela | Zendy; Santos Fustero | Zendy; Mercedes MedioSimón | Zendy

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Diastereoselectivity of the Addition of Propargylic Magnesium Reagents to Fluorinated Aromatic Sulfinyl Imines

Author(s) -

Alberto Llobat,

Jorge Escorihuela,

Santos Fustero,

Mercedes MedioSimón

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01076

Subject(s) - chemistry , reagent , aryl , magnesium , selectivity , bromide , combinatorial chemistry , organic chemistry , magnesium bromide , medicinal chemistry , catalysis , alkyl

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.

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