Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives
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Regioselective a-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxo-thiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.
Keywords:thiazolidines / halogenation / regiochemistry / rearrangement
Source:Tetrahedron, 2001, 57, 27, 5833-5841
- Pergamon-Elsevier Science Ltd, Oxford