The first enantioselective synthesis of the amino acid, (2S,3S,4R)-γ-hydroxyisoleucine using a palladium(ii) catalysed 3,3-sigmatropic rearrangement,10.1039/B401076K

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The first enantioselective synthesis of the amino acid, (2S,3S,4R)-γ-hydroxyisoleucine using a palladium(ii) catalysed 3,3-sigmatropic rearrangement

Andrew G. Jamieson,Andrew Sutherland,Christine L. Willis

Organic & Biomolecular Chemistry Pub Date : 02/19/2004 00:00:00 , DOI:10.1039/B401076K

Abstract

A synthetic route towards the synthesis of (2S,3S,4R)-γ-hydroxyisoleucine, the amino acid component of the natural product, funebrine has been developed using as the key step, a palladium(II) catalysed 3,3-sigmatropic rearrangement to create the (2S)-stereogenic centre.