An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine

An efficient, practical asymmetric synthesis of (R)-norfluoxetine 1 and (R)-fluoxetine 2 has been achieved. The synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the common building block 1,3-amino alcohol 9, from which (R)-norfluoxetine, (R)-fluoxetine and other related analogs can be synthesized. (C) 2002 Elsevier Science Ltd. All rights reserved.