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Synthesis of (-)-Cytisine Using a 6- endo aza-Michael Addition.

著者 Barát V , Csókás D , Bates RW
J Org Chem.2018 08 17 ; 83(16):9088-9095.
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An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6- endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.
PMID: 29998734 [PubMed]
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