01399nas a2200265 4500008004100000022001400041245008900055210006900144260010600213300001400319490000700333520039800340653002800738653002700766653002800793653002500821653002800846100002400874700002400898700002400922700002300946700002400969700002400993856011601017 2014 eng d a0040-403900aChiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid0 aChiron approach to formal synthesis of both antipodes of cis 3hy aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcNOV a6423-64260 v553 a
The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization and selective N-debenzylation over O-debenzylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.
10a3-Hydroxypipecolic acid10aAziridine ring opening10aAziridine-2-carboxylate10aPiperidine alkaloids10aSelective debenzylation1 aChavan, Subhash, P.1 aKhairnar, Lalit, B.1 aChavan, Prakash, N.1 aDumare, Nilesh, B.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G. uhttp://library.ncl.res.in/content/chiron-approach-formal-synthesis-both-antipodes-cis-3-hydroxypipecolic-acid-0