Opposite Enantiomers from Minor Enantiomer Recycling and Dynamic Kinetic Resolution Using a Single Biocatalyst

• A one-pot recycling procedure comprising Lewis acid catalyzed enantioselective addition of acetyl cyanide to (E)-2-butenal to give the O-acetylated cyanohydrin and enzyme-catalyzed conversion of the minor product enantiomer back to (E)-2-butenal provided essentially enantiopure (2R,3E)-2-acetoxy-3-pentenenitrile in close to quantitative yield. The opposite enantiomer was obtained, albeit in lower yield and with lower enantiomeric purity than that observed from the minor enantiomer recycling, by dynamic kinetic resolution consisting of reversible addition of HCN to the aldehyde coupled to enzyme-catalyzed acetylation of the cyanohydrin.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

Aldehydes

Cyanoacetylation

Enzyme catalysis

Lewis acids

Titanium

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