Tributyltin Hydride Addition to Nitroalkenes: A Convenient Procedure for the Conversion of Nitroalkenes into Nitroalkanes and Carbonyl Compounds

Article abstract of DOI:10.1021/jo00294a020

A new procedure for the reduction of nitroalkenes by using n-tributyltin hydride as reducing agent is desribed.The reaction proceeds under almost neutral conditions and works well even in the presence of other reduceable functionalities.Hydrolysis and Nef reaction of the resulting nitronates furnished nitroalkanes and carbonyl compounds respectively in high yields.Application of this methodology to the preparation of β-lactam building blocks is also made.