title: A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions.
abstract: 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 strainedtrans-configured bicyclo[3.3.0]skeleton.
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University, Linz, Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Mario
authors.initials: M
authors.lastname: Waser
authors.affiliation: Institute of Analytical Chemistry, Johannes Kepler University, Linz, Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Manuela
authors.initials: M
authors.lastname: Haunschmidt
authors.affiliation: Institute of Analytical Chemistry, Johannes Kepler University, Linz, Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Markus
authors.initials: M
authors.lastname: Himmelsbach
keywords: Cyclization; Mass spectrometry; Molecular modeling; Organocatalysis; Oxidation; Tartaric acid