Nozaki‐Hiyama‐Kishi Reaction

Abstract

The chromium‐promoted coupling between a halide and a carbonyl compound is often known as the Nozaki–Hiyama–Kishi reaction. An intramolecular version of this reaction to afford a cyclic product is generally called the Nozaki–Hiyama–Kishi cyclization. Overall special features and weaknesses of this reaction have been discussed. It has been reported that when a bromofluoroalkene is applied as the nucleophile, only ( E )‐bromofluoroalkene couples with the aldehyde, giving moderate to good yields. When γ‐monosubstituted allylhalides are used as the nucleophiles, the corresponding homoallyl alcohols form with an excellent anti selectivity, regardless of the original configuration of the allyl halides. Other catalytic conditions and uses of chiral ligands have been discussed for this reaction. This reaction is useful for the synthesis of the natural products.