ArticleSynthesis of (2S,4S,5S)-5-hydroxy-4-methylpipecolic acid via amide methylenation of 5-hydroxy-4-methyl-2-piperidinone with dimethyltitanocene

Add time:09/08/2019    Source:sciencedirect.com

(4S,5S)-5-hydroxy-4-methylpiperidine-2-one 4, readily available from S-glutamic acid, serves as a starting material for the synthesis of (2S,4S,5S)-5-hydroxy-4-methylpipecolic acid 12. The key step of this reaction sequence is the chemoselective methylenation of the amide carbonyl group of 6 with dimethyltitanocene to the exocyclic enecarbamate 7. Hydroboration/oxidation of the double bond resulted in the formation of all-cis alcohol 8 which was transformed via aldehyde to 12.

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