Journal
ORGANIC LETTERS
Volume 3, Issue 21, Pages 3377-3379Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol016603c
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[GRAPHICS] The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylldene 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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