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

Viktor Barát; Dániel Csókás; Roderick W. Bates

doi:10.1021/acs.joc.8b01156

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

Viktor Barát, Dániel Csókás, Roderick W. Bates^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	9088-9095
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	83
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.8b01156
Publication status	Published - Aug 17 2018
Externally published	Yes

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© Copyright 2018 American Chemical Society.

ASJC Scopus Subject Areas

Organic Chemistry

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abstract = "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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AU - Csókás, Dániel

AU - Bates, Roderick W.

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N2 - 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.

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

Abstract

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ASJC Scopus Subject Areas

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