Catalytic Asymmetric Synthesis of Piperidines from Pyrrolidine: Concise Synthesis of L-733,060

Catalytic Asymmetric Synthesis of Piperidines from Pyrrolidine: Concise Synthesis of L-733,060

Catalytic asymmetric deprotonation-aldehyde trapping-ring expansion from a 5- to a 6-ring delivers a concise route to each stereoisomer of β-hydroxy piperidines starting from N-Boc pyrrolidine. The methodology is utilized in a 5-step catalytic asymmetric synthesis of the neorokinin-1 receptor antago...

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Veröffentlicht in:Organic letters 2009-05, Vol.11 (9), p.1935-1938
Hauptverfasser: Bilke, Julia L, Moore, Stephen P, O’Brien, Peter, Gilday, John
Format: Artikel
Sprache:eng
Schlagworte:
Molecular Structure
Neurokinin-1 Receptor Antagonists
Piperidines - chemical synthesis
Piperidines - chemistry
Pyrrolidines - chemistry
Stereoisomerism
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Zusammenfassung:Catalytic asymmetric deprotonation-aldehyde trapping-ring expansion from a 5- to a 6-ring delivers a concise route to each stereoisomer of β-hydroxy piperidines starting from N-Boc pyrrolidine. The methodology is utilized in a 5-step catalytic asymmetric synthesis of the neorokinin-1 receptor antagonist, (+)-L-733,060.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900366m