A highly enantioselective deprotonation of cis-4-aminocyclopentene oxide derivatives 1 was achieved by using a chiral lithium amide, prepared from (2S,3aS,7aS)-2-(pyrrolidin-1-ylmethyl) octahydroindole, (1S,4R)-4-Amino-2-cyclopentenol derivative 2 was obtained in up to 90 % ee. (C) 1999 Elsevier Science Ltd. All rights reserved.