A Convenient Method for 3-Pyrroline Synthesis

The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylidene carbene CH-insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary ste...

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Bibliographic Details
Published in:Organic letters 2001-10, Vol.3 (21), p.3377-3379
Main Authors: Green, Martin P, Prodger, Jeremy C, Sherlock, Alexandra E, Hayes, Christopher J
Format: Article
Language:English
Subjects:
Acetylcysteine - analogs & derivatives
Acetylcysteine - chemical synthesis
Alkylation
Anti-Bacterial Agents - chemical synthesis
Combinatorial Chemistry Techniques
Cyclization
Lactams
Pyrroles - chemical synthesis
Stereoisomerism
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Summary:The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylidene carbene CH-insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary stereocenters is a relatively facile process. The insertion reaction occurs with >95% retention of stereochemistry, but the presence of protecting groups on nitrogen is generally deleterious to the cyclization process.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016603c