Synthesis of 1,4- and 1,5-Amino Alcohols via Nucleophilic Addition of Semicyclic N,O-Acetal with Organozinc Reagents.

An efficient approach to access functionalized 1,4- and 1,5-amino alcohols has been developed through the nucleophilic addition of semicyclic N,O-acetal with organozinc reagents. A number of substituted benzyl zinc reagents (including nitrile and ester substituted) could react with semicyclic N,O-acetals 1 and 2, affording the desired products 3a-3p and 4a-4o in good to excellent yields.