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Parallel Recognition by Kinetic Control with Imino Aldehyde Substrates that are Prone to Redistribution
Author(s) -
Orita Akihiro,
Nagano Yoshifumi,
Nakazawa Koichi,
Otera Junzo
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200207)344:5<548::aid-adsc548>3.0.co;2-a
Subject(s) - chemistry , aldehyde , redistribution (election) , imine , catalysis , substrate (aquarium) , kinetic control , combinatorial chemistry , aldimine , diene , organic chemistry , oceanography , natural rubber , geology , politics , political science , law
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.