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Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones

✍ Scribed by Guillaume Burtin; Pierre-Jean Corringer; Peter B. Hitchcock; Douglas W. Young

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
258 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Oxazinones have been synthesised and used as chiral templates in the synthesis of I~substituted aspartic acids. Use of a Bredmvck's reagent/Grigaard/hydrogenation strategy gave c/soxazinones with complete stereoseleetivity, whereas an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones could be converted to 13-substituted aspartic acids and to regioselectively protected l~-substitoted aspartic acids without loss of stereoche~stry at either centre.

📜 SIMILAR VOLUMES

Synthesis of Substituted 2-Amino-6H-1,3-
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