Cyanohydrin reaction explained

A cyanohydrin reaction is an organic chemical reaction in which an aldehyde or ketone reacts with a cyanide anion or a nitrile to form a cyanohydrin. This nucleophilic addition is a reversible reaction but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products. The cyanide source can be potassium cyanide, sodium cyanide or trimethylsilyl cyanide. With aromatic aldehydes such as benzaldehyde, the benzoin condensation is a competing reaction. The reaction is used in carbohydrate chemistry as a chain extension method for example that of D-xylose.

Asymmetric synthesis

The asymmetric cyanohydrin reaction of benzaldehyde with trimethylsilylcyanide is made possible by employment of (R)-Binol[1] at 1–10% catalyst loading. This ligand firsts reacts with a lithium alkoxy compound to form a lithium binaphtholate Complex.

The chemist Urech in 1872 was the first to synthesize cyanohydrins from ketones with alkali cyanides and acetic acid[2] and therefore this reaction also goes by the name of Urech cyanohydrin method.

External links

Notes and References

  1. Chiral Lithium Binaphtholate Aqua Complex as a Highly Effective Asymmetric Catalyst for Cyanohydrin Synthesis . Manabu . Hatano . Takumi . Ikeno . Takashi . Miyamoto . Kazuaki . Ishihara . . 2005 . 127 . 31 . 10776–77 . 10.1021/ja051125c. 16076152 .
  2. Urech . Friedrich . Ueber einige Cyanderivate des Acetons . . 164 . 255 . 1872 . 2 . 10.1002/jlac.18721640207.

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