TY - JOUR T1 - Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid JF - Tetrahedron Letters Y1 - 2014 A1 - Chavan, Subhash P. A1 - Khairnar, Lalit B. A1 - Chavan, Prakash N. A1 - Dumare, Nilesh B. A1 - Kalbhor, Dinesh B. A1 - Gonnade, Rajesh G. KW - 3-Hydroxypipecolic acid KW - Aziridine ring opening KW - Aziridine-2-carboxylate KW - Piperidine alkaloids KW - Selective debenzylation AB -

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.

PB - PERGAMON-ELSEVIER SCIENCE LTD CY - THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND VL - 55 IS - 47 U3 - Foreign U4 - 2.347 ER -