Amino-Protecting Reagents: New Promising Reagents for tert-Butoxycarbonylation, Benzyloxycarbonylation, and carbonylation

Article abstract of DOI:10.1021/jo00135a003

A new method for the preparation of tert-butyl- (1d), benzyl- (1e), and (β-trimethylsilyl)ethyl α-methoxyvinyl carbonates (1f) has been devised.The reaction of these reagents with amino compounds proceeds rapidly under mild conditions to give the corresponding N-tert-butoxycarbonylated (N-Boc), N-benzyloxycarbonylated (N-Z), and N-<β-(trimethylsilyl)ethoxy>carbonylated (N-Tmseoc) compounds in quantitative yields.Twenty-two examples using amines, amino alcohols, and amino acids were presented.