Journal of Organic Chemistry p. 9088 - 9095 (2018)
Update date:2022-09-26
Topics:
Barát, Viktor
Csókás, Dániel
Bates, Roderick W.
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.
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