Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid

Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid

[Display omitted] The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization a...

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Veröffentlicht in:Tetrahedron letters 2014-11, Vol.55 (47), p.6423-6426
Hauptverfasser: Chavan, Subhash P., Khairnar, Lalit B., Chavan, Prakash N., Dumare, Nilesh B., Kalbhor, Dinesh B., Gonnade, Rajesh G.
Format: Artikel
Sprache:eng
Schlagworte:
3-Hydroxypipecolic acid
Antipodes
Aziridine ring opening
Aziridine-2-carboxylate
Chiron
Enantiomers
Piperidine alkaloids
Precursors
Ring opening
Selective debenzylation
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:[Display omitted] The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization and selective N-debenzylation over O-debenzylation reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.09.118