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Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization.

Organic & biomolecular chemistry (2010-07-28)
Lahssen El Blidi, Nicolas Vanthuyne, Didier Siri, Stéphane Gastaldi, Michèle P Bertrand, Gérard Gil
ABSTRAKT

Chemoenzymatic dynamic kinetic resolution (DKR) of amines involving sulfanyl radical-induced racemization happened to be the very first switchable DKR process allowing the synthesis of either (R)- or (S)-amides, in good yield and high enantiomeric excess, depending on the nature of the enzyme; the different steps of the development of (S)-selective DKR are discussed.

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Sigma-Aldrich
2,2′-Azobis(2-methylpropionitrile) solution, 0.2 M in toluene