@article{HellerHerdeis1993,
  author    = {Heller, Eberhard and Herdeis, Claus},
  title     = {Synthesis of 2S,5S- and 2R,5S-5-Hydroxypipecolic Acid via Amide-Methylenation of S-5-Hydroxy-2-piperidone with Dimethyltitanocene},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-38288},
  year      = {1993},
  abstract  = {A route to 2S,5S-and 2R,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselsctive methylenation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The transformation of the exocyclic enecarbamate double bond to the carboxylic acid group is best accomplished via hydroboration/oxidation to the alcohol 11a,b. Separation and oxidation of the dlastereomers 11a,b, to 148. and 14b, and hydrolysis furnishes the diastereomeric pipecolic acids 15a and 15b in enantiopure form.},
  subject      = {Chemie},
  language  = {en}
}