866462-69-3Relevant academic research and scientific papers
Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
, p. 6409 - 6416 (2010)
Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright
SYNTHESIS AND BEHAVIOUR OF NADH MODELS BEARING A CHIRAL SULFOXIDE
Boussad, N.,Trefouel, T.,Dupas, G.,Bourguignon, J.,Queguiner, G.
, p. 127 - 138 (2007/10/02)
Chiral 3-sulfinyl-1,4-dihydropyridine derivatives were synthesized by asymmetric oxidation of the parent 3-pyridine sulfides with Kagan's reagent (Ti(OiPr)4/diethyl tartrate/H2O/tBuOOH = 1/2/1/1).The chemoselective oxidation conditions of the sulfur atom were optimized.One chiral NADH mimic reagent so obtained was used in the reduction of prochiral α,α',α''-trifluoroacetophenone.During this reduction a side reaction occurred i.e. desulfenylation of the reagent.The by-product was identified after trapping with methyl propiolate.This side reaction did not occur in the quinoline series.
