1029124-37-5Relevant articles and documents
Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer
Hostmann, Theresa,Molloy, John J.,Bussmann, Kathrin,Gilmour, Ryan
, p. 10164 - 10168 (2019/12/24)
Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.
Highly enantioselective reduction of β,β-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes
Fryszkowska, Anna,Fisher, Karl,Gardiner, John M.,Stephens, Gill M.
, p. 4295 - 4298 (2008/12/20)
(Chemical Equation Presented) This is the first report of the use of Clostridium sporogenes extracts for enantioselective reduction of C=C double bonds of β,β-disubstituted (1) and α,β-disubstituted nitroalkenes (3). Crude enzyme preparations reduced aryl derivatives 1a-e and 1h, in 35-86% yield with ≥97% ee. Reduction of (E)- and (Z)-isomers of 1c gave the same enantiomer of 2c (≥99% ee). In contrast, α,β- disubstituted nitroalkene 3a was a poor substrate, yielding (S)-4a in low yield (10-20%), and the ee (30-70% ee) depended on NADH concentration. An efficient synthesis of a library of nitroalkenes 1 is described.
