Highly Diastereoselective Zinc-Catalyzed Propargylation of tert-Butanesulfinyl Imines

A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthe...

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Bibliographic Details
Published in:Organic letters 2010-02, Vol.12 (4), p.748-751
Main Authors: Fandrick, Daniel R, Johnson, Courtney S, Fandrick, Keith R, Reeves, Jonathan T, Tan, Zhulin, Lee, Heewon, Song, Jinhua J, Yee, Nathan K, Senanayake, Chris H
Format: Article
Language:English
Subjects:
Alkynes
Amines - chemical synthesis
Amines - chemistry
Catalysis
Combinatorial Chemistry Techniques
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Imines - chemistry
Molecular Structure
Propanols
Stereoisomerism
Sulfonium Compounds - chemistry
Zinc - chemistry
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Summary:A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet−Spengler cyclization.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9028258