An efficient prepn. of a series of secondary amines, structurally related to the kainic acid scaffold, is described. Naturally occurring (-)-α-kainic acid was hydroformylated with complete terminal selectivity and high stereoselectivity. The stereochem. of the product was investigated through the ROESY and HETLOC spectra of the corresponding 2,4-dinitrophenylhydrazone, showing the presence of a single diastereoisomer with rotamers related to the presence of the Boc group. The aldehyde was used as a platform to prep. amines by reductive amination in ionic liqs.
Synthesis of kainoids via a highly stereoselective hydroformylation of kainic acid.
RODRIQUEZ, Manuela;BASSARELLO, Carla;BIFULCO, Giuseppe;
2005-01-01
Abstract
An efficient prepn. of a series of secondary amines, structurally related to the kainic acid scaffold, is described. Naturally occurring (-)-α-kainic acid was hydroformylated with complete terminal selectivity and high stereoselectivity. The stereochem. of the product was investigated through the ROESY and HETLOC spectra of the corresponding 2,4-dinitrophenylhydrazone, showing the presence of a single diastereoisomer with rotamers related to the presence of the Boc group. The aldehyde was used as a platform to prep. amines by reductive amination in ionic liqs.File in questo prodotto:
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