A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions
نویسندگان
چکیده
Attempted oxidation of a TADDOL-derived bisthioacetate resulted in a rather unexpected and remarkable cyclization and deprotection reaction, giving a thiolane-1, 1-dioxide as the main product. Systematic in situ ESI-HRMS studies revealed a bicyclic, highly acid labile key intermediate of this reaction. Supported by force field calculations, the high sensitivity of this intermediate was judged to be due to the formation of a highly strained trans-configured bicyclo[3.3.0]skeleton.
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عنوان ژورنال:
دوره 141 شماره
صفحات -
تاریخ انتشار 2010