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Chemija / Chemistry

ISSN 0235-7216
ISSN 2424-4538 (online)

2009 m. Nr. 2

Stereoselective synthesis of 1-amino-5-butyl-3-oxocyclohexane-1-carboxylic acid derivatives
Sonata KRIKŠTOLAITYTĖ, Algirdas ŠAČKUS, Christian RØMMING, Kjell UNDHEIM

Butyl-substituted 1-amino-3-oxocyclohexane-1-carboxylic acid derivatives have been prepared from 5,5-tethered dienes of (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine in stereoselective synthesis. RCM reactions of the diene afforded a heterospirenone which was the substrate for the conjugated addition reaction with lithium dibutylcuprate. Hydrolysis of the adduct provided cyclic α-amino acid derivatives. The absolute configuration at the new stereocentres were established by X-ray analyses.

Keywords: constrained α-amino acids, Schöllkopf’s auxiliary, stereoselective synthesis, ring closing methathesis, X-ray crystal structure

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