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The unsaturated β-amino acid derivatives (3R)-(E)-3-(N-tert- butoxycarbonyl)aminohex-4-enoate and methyl (2S,3S)-3-(N-tert- butoxycarbonyl)-amino-2-bydroxyhex-4-enoate have been synthesised from lithium (s)-(α-methylbenzyl)allylamide and (E,E)-tert-butyl hex-2,4- dienoate. After a highly stereoselective conjugate addition of the lithium amide to the α,β-unsaturated ester, or a highly stereoselective conjugate addition-electrophilic hydroxylation, the adducts are deallylated and the resulting secondary amines converted to either a benzoyl amide or oxazolidinone. The N-α-methylbenzyl group is then removed with either formic acid or using a dissolving metal reduction. These deprotection procedures leave unsaturation in the molecules intact.

Original publication

DOI

10.1016/S0957-4166(97)00470-9

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

23/10/1997

Volume

8

Pages

3387 - 3391