- Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates
-
Michael addition reaction of α-branched aldehydes to β-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, l-phenylalanine, and its lithium salt to give β-formyl-β′-nitroesters having a quaternary carbon centre in good yields (up to 85%) with high enantioselectivity (up to 98% ee). By using benzyl β-nitroacrylates as Michael acceptors, the obtained β-formyl-β′-nitroesters were converted into various 4,4-disubstituted pyrrolidine-3-carboxylic acids including analogues of gabapentin (Neurotin) in one step from the Michael adducts in high yields. The Royal Society of Chemistry 2012.
- Yoshida, Masanori,Masaki, Erika,Ikehara, Hiroto,Hara, Shoji
-
experimental part
p. 5289 - 5297
(2012/08/08)
-
- Branched alkyl pyrrolidine-3-carboxylic acids
-
Branched alkyl pyrrolidines of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropatnological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.
- -
-
-
