A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions

作者：Waser Mario^*; Haunschmidt Manuela; Himmel**ach Markus

来源：Monatshefte fur Chemie, 2010, 141(12): 1347-1351.

DOI：10.1007/s00706-010-0410-5

• Oxidation
• Molecular modeling
• Cyclization
• Mass spectrometry
• Tartaric acid
• Organocatalysis

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.

• 出版日期2010-12