98157-00-7Relevant academic research and scientific papers
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)
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.
A convenient one-pot synthesis and bioactivity of N-dichloroacetyl-5-aryl- 1,3-oxazolidines
Ye, Fei,Liu, Cheng-Guo,Wang, Xin-Ming,Fu, Ying,Gao, Shuang
, p. 201 - 205 (2013/09/02)
New N-dichloroacetyl-5-aryl-1,3-oxazolidines 4 were synthesized by cycloaddition reaction of an aryl substituted hydroxyalkylamine 1 with aldehyde or ketone 2, followed by acylation, without isolation of the intermediate product 3. The structures of compounds 4 were determined by spectral and elemental analyses. The structure of 4b was determined by an X-ray crystallographic analysis. The bioassay results demonstrate that these compounds could alleviate chlorsulfuron injury to maize.
