73712-54-6Relevant articles and documents
Parallel Recognition by Kinetic Control with Imino Aldehyde Substrates that are Prone to Redistribution
Orita, Akihiro,Nagano, Yoshifumi,Nakazawa, Koichi,Otera, Junzo
, p. 548 - 555 (2007/10/03)
One-shot treatment of a mixture of Danishefsky diene 4 and tetraallyltin 8 with 3-formylbenzylidene imines 1 in the presence of Sc(OTf)3 catalyst provides a single product 13 as a result of exclusive Diels-Alder and allylation reactions on the imine and aldehyde functions, respectively. The chemoselectivities of the respective elementary reactions are improved in the parallel reaction, and the redistribution of substrate 1 that is induced readily by Sc(OTf)3 is completely suppressed, thus offering a novel protocol for simplification of the multi-step chemical process.