Journal
SYNLETT
Volume 28, Issue 11, Pages 1300-1304Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588718
Keywords
organocatalysis; bifunctional catalyst; noncovalent interaction; asymmetric cyclization; chiral oxazoline
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Funding
- Science and Technology Innovation Committee of Shenzhen Municipality [JCYJ20160226105602871]
- China Postdoctoral Science Foundation [2016M590009]
- Guangdong Province Special Branch Program [2014TX01R111]
- Natural Science Foundation of Guangdong Province [2016A030310243]
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An enantioselective [3+2] cyclization is reported for the construction of a chiral oxazoline skeleton in moderate yield and up to 97% ee. The reactivity and stereochemical discrimination originate from the noncovalent interaction and orientation of a bifunctional catalyst. The novel combination of an alpha-keto ester and an alpha-isocyanoacetate establishes an oxazoline which could be a potential chiral ligand for metalmediated catalysis, and also could be easily converted into an optically active beta-hydroxy-alpha-amino acid.
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