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; GOMEZ PALOMA, Luigi; Mann, Andre; Marchetti, Mauro; Schoenfelder, Angele; Taddei, Maurizio. - In: SYNLETT. - ISSN 0936-5214. - 10:(2005), pp. 1581-1585. [10.1055/s-2005-869835]
Synthesis of kainoids via a highly stereoselective hydroformylation of kainic acid
RODRIQUEZ, Manuela;
2005
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 | Dimensione | Formato | |
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