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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Bibliographic Details
Published in:Organic letters Vol. 11; no. 9; pp. 1935 - 1938
Main Authors: Bilke, Julia L, Moore, Stephen P, O’Brien, Peter, Gilday, John
Format: Journal Article
Language:English
Published: United States American Chemical Society 07-05-2009
Subjects:
Molecular Structure
Neurokinin-1 Receptor Antagonists
Piperidines - chemical synthesis
Piperidines - chemistry
Pyrrolidines - chemistry
Stereoisomerism
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900366m