180675-07-4Relevant articles and documents
Practical synthesis of both enantiomers of protected 4-oxopipecolic acid
Machetti, Fabrizio,Cordero, Franca M,De Sarlo, Francesco,Brandi, Alberto
, p. 4995 - 4998 (2007/10/03)
A new synthesis of both enantiomers of protected 4-oxopipecolic acid was achieved in six steps via 1,3-dipolar cycloaddition of C-ethoxycarbonyl N-(1R)-phenylethylnitrone to but-3-en-1-ol.
A new synthesis of (2S)-4-oxopipecolic acid by thermal rearrangement of enantiopure spirocyclopropaneisoxazolidine
Machetti, Fabrizio,Cordero, Franca M.,De Sarlo, Francesco,Guarna, Antonio,Brandi, Alberto
, p. 4205 - 4208 (2007/10/03)
A novel synthesis of (2S)-4-oxo-pipecolic acid is reported. The synthetic route employs as a key step the diastereoselective cycloaddition of the N- glycosylnitrone 7 to methylenecyclopropane followed by thermal rearrangement of the spirocyclopropaneisoxazolidine 8a. Stereoselective reduction of the N- BOC methyl ester of 4-oxopipecolic acid by L-selectride gives the protected cis-4-hydroxy-pipecolic acid 14.