Diastereoselective Cycloaddition of Allyltrialkylsilanes to Intermediate N-Acyliminoesters Obtained from Methyl 4-Methoxy-2-Imidazolidinone- and 2-Oxazolidinone-4-carboxylates

Article abstract of DOI:10.1016/0040-4039(94)85317-7

The amidoalkylation reaction of methyl 4-methoxy-2-imidazolidinone-4-carboxylates or methyl 4-methoxy-2-oxazolidinone-4-carboxylates using allylsilanes as nucleophiles in the presence of TiCl4 affords three carbon ring annulation products 5 and 9 via a <3+2> cycloaddition.Besides that, the simple methoxy group substitution product is formed.The ring annulation occurs with practically total diastereoselectivity so that all substituents are located on the β-side of the bicyclic product.