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Synlett 2005(10): 1581-1585
DOI: 10.1055/s-2005-869835
DOI: 10.1055/s-2005-869835
LETTER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Kainoids via a Highly Stereoselective Hydroformylation of Kainic Acid
Further Information
Received
15 March 2005
Publication Date:
10 May 2005 (online)
Publication History
Publication Date:
10 May 2005 (online)

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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