Tetrahedron: Asymmetry

Sharpless asymmetric dihydroxylation as the key step in the enantioselective synthesis of spirocyclic σ 1 receptor ligands

K Holl, D Schepmann, CG Daniliuc, B Wuensch

Index: Holl, Katharina; Schepmann, Dirk; Daniliuc, Constantin Gabriel; Wuensch, Bernhard Tetrahedron Asymmetry, 2014 , vol. 25, # 3 p. 268 - 277

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Citation Number: 3

Abstract

Abstract The enantioselective synthesis of fluorinated spirocyclic σ 1 ligands involved three key steps:(1) the Sharpless asymmetric dihydroxylation of 2-bromostyrene 5 provided enantiomerically pure diols (R)-6 and (S)-6 establishing the stereogenic center;(2) the intramolecular opening of the oxirane ring of (R)-11 and (S)-11, which occurred with excellent regioselectivity and complete inversion of configuration giving access to ...