Processing of Cyclopropylarenes by Toluene Dioxygenase: Isolation and Absolute Configuration of Metabolites.

Abstract

Microbiological syntheses O 0035Processing of Cyclopropylarenes by Toluene Dioxygenase: Isolation and Absolute Configuration of Metabolites. -A series of cyclopropyl substituted arenes is subjected to enzymatic oxidation in order to obtain novel synthons for asymmetric synthesis (yields given in mg/l). -(FINN, K. J.; ROCHON, L.; HUDLICKY*, T.; Tetrahedron: Asymmetry 16 (2005) 21, 3606-3613; Dep. Chem., Brock Univ., St. Catharines, Ont. L2S 3A1, Can.; Eng.) -Nuesgen 14-044

New Options for the Reactivity of the Burgess Reagent with Epoxides in Both Racemic and Chiral Auxiliary Modes – Structural and Mechanistic Revisions, Computational Studies, and Application to Synthesis

“…[23] In 2006 we published a preliminary report on the synthesis of enantiopure sulfamidates and the corresponding trans amino alcohols in both enantiomeric forms by employing a chiral auxiliary version of the Burgess reagent, the menthyl carbamate 10, Figure 4. Prior to this report we also prepared several other chiral auxiliary versions such as the camphor-derived carbamate 11 and the two cyclic forms 12 and 13 prepared from the diene diol 14; [24] however, the reactions of these reagents with oxiranes proved erratic, and we therefore focused on the investigations of reactions of the menthyl version. We prepared the menthyl carbamate version of the reagent 10 despite expectations that a freely rotating auxiliary group might not lead to significant levels of diastereoselection.…”