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Synlett 2005(10): 1581-1585  
DOI: 10.1055/s-2005-869835
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Kainoids via a Highly Stereoselective Hydroformylation of Kainic Acid

Manuela Rodriqueza, Carla Bassarellob, Giuseppe Bifulcob, Luigi Gomez-Palomab, André Mannc, Mauro Marchettid, Angèle Schoenfelderc, Maurizio Taddei*a
a Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro, 53100 Siena, Italy
Fax: +39(0577)234333; e-Mail: taddei.m@unisi.it;
b Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte don Melillo, 84084 Fisciano, Salerno, Italy
c Laboratoire de Pharmacochimie de la Communication Cellulaire, UMR 7081, Faculté de Pharmacie, Route du Rhin, 67401 Illkirch, ­France
d CNR, Istituto di Chimica Biomolecolare, sez. Sassari, trav. La Crucca, 3, 07040 Li Punti, Sassari, Italy
Further Information

Publication History

Received 15 March 2005
Publication Date:
10 May 2005 (online)

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Abstract

An efficient preparation 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 stereochemistry of the product was investigated through the ROESY and HETLOC spectra of the corresponding 2,4-dinitrophenyl hydrazone, 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 prepare amines by reductive amination in ionic liquids.

Key words

hydroformylation - natural products - ionic liquids - ­heterocycles

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