Nucleophilic addition of organocerium reagents to alpha-alkoxy hydrazones:A new type of elimination reaction to alpha-hydroxynitriles

We studied the nucleophilic addition of organoceriun reagents to alpha-alko xy hydrazones. The results depend upon the organocerium reagents, the natur e of protection for the hydroxy group, and the solvents used. Contrary to G rignard reagents, organocerium reagents derived from Grignard reagents effe ctively add to alpha-alkoxy hydrazones. In addition, a new type of eliminat ion reaction of alpha-alkoxy hydrazones to the corresponding nitriles by me thyl chloroformate was found. This methodology is an efficient and potentia lly practical synthetic route to beta-hydroxy amines. (C) 2000 John Wiley & Sons, Inc.