Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization | Zendy

Qiang Wang | Zendy; Marvin Lübcke | Zendy; Maria Biosca | Zendy; M. Hedberg | Zendy; Lars Eriksson | Zendy; Fahmi Himo | Zendy; Kálmán J. Szabó | Zendy

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Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization

Author(s) -

Qiang Wang,

Marvin Lübcke,

Maria Biosca,

M. Hedberg,

Lars Eriksson,

Fahmi Himo,

Kálmán J. Szabó

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c09323

Subject(s) - stereocenter , chemistry , enantioselective synthesis , nucleophile , fluorine , catalysis , organocatalysis , stereoselectivity , carbon fibers , organic chemistry , fluoride , combinatorial chemistry , inorganic chemistry , materials science , composite number , composite material

1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with in situ generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to investigate the details of the mechanism and the factors governing the stereoselectivity of the reaction.

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