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Synthesis of Highly Enantio-Enriched α-Amino Acids by Carboxylation of N-(α-Lithioalkyl)oxazolidinones

✍ Scribed by Fabien Jeanjean; Guy Fournet; Didier Le Bars; Jacques Goré

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 350 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200004)2000:7<1297::aid-ejoc1297>3.0.co;2-l

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✦ Synopsis

N-(α-Stannylalkyl)

oxazolidinones can be obtained as a mixture of diastereomers in three steps from aldehydes with yields dependent on the R group of R-CHO. They can be transformed by a tin-lithium exchange to N-(α-lithioalkyl)oxazolidinones which equilibrate rapidly to one diastereomer. These compounds give rise, after carboxylation, to the diastereopure N-(α-carboxyalkyl)oxazolidinones. Transforma- [a] Laboratoire de chimie organique 1, associe ´au CNRS, bat. 308

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