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PubMed · 11594838

A convenient method for 3-pyrroline synthesis.

M P Green·J C Prodger·A E Sherlock·C J Hayes
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Abstract

[reaction: see text]. 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.

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AcetylcysteineAlkylationAnti-Bacterial AgentsCombinatorial Chemistry TechniquesCyclizationLactamsPyrrolesStereoisomerismJournal ArticleResearch Support, Non-U.S. Gov't

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M P Green, J C Prodger, A E Sherlock, C J Hayes. 2001-10-18. A convenient method for 3-pyrroline synthesis.. https://doi.org/10.1021/ol016603c

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