Nucleophilic addition of organocerium reagents to α‐alkoxy hydrazones: A new type of elimination reaction to α‐hydroxynitriles

We studied the nucleophilic addition of organocerium reagents to α‐alkoxy hydrazones. The results depend upon the organocerium reagents, the nature of protection for the hydroxy group, and the solvents used. Contrary to Grignard reagents, organocerium reagents derived from Grignard reagents effectively add to α‐alkoxy hydrazones. In addition, a new type of elimination reaction of α‐alkoxy hydrazones to the corresponding nitriles by methyl chloroformate was found. This methodology is an efficient and potentially practical synthetic route to β‐hydroxy amines. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:65–72, 2000