434936-23-9Relevant academic research and scientific papers
Lithiation and stereoselective transformations of 3-aroyl-2,2,4,4tetramethyloxazolidines (TMO amides), a new class of acid-labile atropisomeric amides
Anstiss, Mark,Clayden, Jonathan,Grube, Alexander,Youssef, Latifa H.
, p. 290 - 294 (2007/10/03)
Aromatic amides 4 (3-aroyl-2,2,4,4-tetramethyloxazolidines or TMO amides) derived by acylation of 2,2,4,4-tetramethyloxazolidine 6 undergo ortho- and lateral lithiation reactions. Given sufficient steric hindrance to bond rotation, they exhibit atropisomerism about the Ar-CO bond and the Ar-CO axis is able to control the atroposelective formation of new stereogenic centres. Unlike amides derived from hindered secondary amines such as diisopropylamine, the 3-aroyl-2,2,4,4-tetramethyloxazolidines are acid-sensitive, and treatment with methanesulfonic acid gives lactones or lactams by cyclisation onto the amide group.
