Kinetic Resolution of Amines: A Highly Enantioselective and Chemoselective Acetylating Agent with a Unique Solvent‐Induced Reversal of Stereoselectivity | Zendy

Arseniyadis Stellios | Zendy; Valleix Alain | Zendy; Wagner Alain | Zendy; Mioskowski Charles | Zendy

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Kinetic Resolution of Amines: A Highly Enantioselective and Chemoselective Acetylating Agent with a Unique Solvent‐Induced Reversal of Stereoselectivity

Author(s) -

Arseniyadis Stellios,

Valleix Alain,

Wagner Alain,

Mioskowski Charles

Publication year - 2004

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200453956

Subject(s) - stereoselectivity , enantioselective synthesis , chemistry , solvent polarity , toluene , solvent , kinetic resolution , combinatorial chemistry , organic chemistry , catalysis

Solvents lend a hand : Changing the polarity of the reaction solvent from 1,3‐dimethyltetrahydropyrimidin‐2‐one (DMPU) to toluene reverses the stereoselectivity observed in the acetylation of amines with (1 S ,2 S )‐ 1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90 % ee ( S ) in DMPU at −20 °C with a 33 % conversion.

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