The acylative dimerisation of 2-alkenyl-1,3-thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single double-bond isomer. The scope of the reaction has been evaluated synthetically, while a computational study has elucidated the mechanism of the reaction and the origin of stereocontrol. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
- semiempirical calculations
- DIELS-ALDER REACTIONS