2745-22-4Relevant articles and documents
Trichloronitromethane with acyl chlorides in the presence of tin(II) chloride: Synthesis of trichloronitro ketones
Demir,Tanyeli,Aksoy,Gulbeyaz,Mahasneh
, p. 1071 - 1073 (1995)
Trichloronitromethane adds to acid chlorides in the presence of tin(II) chloride to yield dichloronitro ketones via a substitution reaction. Reduction and dechlorination of the dichloronitro ketones give dichloroamino alcohols and nitro ketones, respectiv
One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols
Schrittwieser, Joerg H.,Coccia, Francesca,Kara, Selin,Grischek, Barbara,Kroutil, Wolfgang,D'Alessandro, Nicola,Hollmann, Frank
, p. 3318 - 3331 (2013/12/04)
One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.
Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose
Haukaas, Michael H.,O'Doherty, George A.
, p. 3899 - 3902 (2007/10/03)
equation presented The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars.
