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, M., Bassarello, C., Bifulco, G., GOMEZ PALOMA, L., Mann, A., Marchetti, M., Schoenfelder, A., Taddei, M.. - 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 | |
|---|---|---|---|
|
SYNLETT 2005, No. 10, pp 1581–1585.pdf
non disponibili
Dimensione
104.01 kB
Formato
Adobe PDF
|
104.01 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
