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11.2: Formation of Carbon-Carbon Bonds

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    Biocatalysts are turned out to be versatile catalysts for carbon-carbon bond forming and reduction reactions in organic synthesis.

    Carbon-carbon bond formation belongs to the heart of organic synthesis. The biocatalyzed route provides effective tool for the construction of carbon-carbon with excellent enantioselectivity.

    Hydrocyanation of Aldehydes

    The biocatalytic hydrocyanation of aldehydes is one of the oldest methods in organic synthesis. One of the well-established technologies for the large-scale hydrocyanation of aldehydes is the oxynitrilase (Griengl process) catalyzed production of (S)-phenoxybenzaldehyde cyanohydrins, which is an important intermediate for the industrial pyrethroid manufacture (Scheme \(\PageIndex{1}\)). This method is turned out to be useful for the reactions of numerous aldehydes.

    clipboard_e28c191dd162f98247ac0b68df3d1f9e3.png
    Scheme \(\PageIndex{1}\)

    Benzoin Condensation

    The development of an asymmetric cross-benzoin condensation via enzymatic cross-coupling reactions is a synthetically useful process. Highly enantiomerically enriched mixed benzoins can be obtained from two different substituted benzaldehdyes using benzaldehyde lyase as a catalyst (Scheme \(\PageIndex{2}\)). One of the aldehydes acts as acceptor, whereas the other one acts as donor.

    clipboard_ea4e1a20669034b1ae4c247d94dc3466e.png
    Scheme \(\PageIndex{2}\)

    Aldol Reaction

    The biocatalytic aldol reactions are highly specific with respect to donor component, whereas a broad substrate scope is observed for the acceptor molecules. One of the examples is the reaction of glycine (donor) with substituted benzaldehyde (acceptor) employing threonine aldolases to give α-amino β -hydroxy acids with excellent enantioselectivity (Scheme \(\PageIndex{3}\)).

    clipboard_ea3f86d3d7635c87af2a0a1c7b16e889e.png
    Scheme \(\PageIndex{3}\)

    Nitroaldol Reaction

    Enzymes are also useful for the non-natural reactions. For example, using (S)-oxynitrilase the reaction of nitromethane with a broad range of aldehydes can be accomplished with excellent enantioselectivity (Scheme \(\PageIndex{4}\)). Nitroalkane acts donor, whereas the aldehydes are acceptors.

    clipboard_e0a0f1b28c6d8cb3672e43f6963a86404.png
    Scheme \(\PageIndex{4}\)

    This page titled 11.2: Formation of Carbon-Carbon Bonds is shared under a CC BY-SA license and was authored, remixed, and/or curated by Tharmalingam Punniyamurthy (National Programme on Technology Enhanced Learning (NPTEL) ) .

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