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Direct Access to Cumbersome Aminated Quaternary Centers by Hyperbaric Aza‐Michael Additions
Author(s) -
Rulev Alexander Yu.,
Azad Saleha,
Kotsuki Hiyoshizo,
Maddaluno Jacques
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000984
Subject(s) - chemistry , michael reaction , alkyl , quaternary carbon , amine gas treating , catalysis , organic chemistry , primary (astronomy) , tertiary amine , quaternary , medicinal chemistry , polymer chemistry , combinatorial chemistry , enantioselective synthesis , paleontology , physics , astronomy , biology
Abstract The aza‐Michael addition of secondary amines to α,β‐ or β,β‐disubstituted α,β‐unsaturated esters was efficiently achieved under high pressure (10–16 kbar) in protic solvents in the absence of any catalyst. The expected cumbersome β‐aminoesters bearing a tertiary amine directly connected to a quaternary carbon atom could be isolated in fair to good yields. By using α,β,δ,γ‐unsaturated esters (alkyl sorbate), the addition took place regioselectively in a 1,6 manner and afforded the β,γ‐unsaturated δ‐aminoesters.