A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions.
作者： Mario Waser , Manuela Haunschmidt , Markus Himmelsbach
DOI: 10.1007/S00706-010-0410-5
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摘要: Attempted oxidation of a TADDOL-derived bisthioacetate resulted in rather unexpected and remarkable cyclization deprotection reaction, giving thiolane-1, 1-dioxide as the main product. Systematic situ ESI-HRMS studies revealed bicyclic, highly acid labile key intermediate this reaction. Supported by force field calculations, high sensitivity was judged to be due formation strained trans-configured bicyclo[3.3.0]skeleton.
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