1186497-23-3Relevant articles and documents
Production of (S)-β-Nitro Alcohols by Enantioselective C?C Bond Cleavage with an R-Selective Hydroxynitrile Lyase
Rao, D. H. Sreenivasa,Padhi, Santosh Kumar
, p. 371 - 378 (2019/01/08)
Hydroxynitrile lyase (HNL)-catalysed stereoselective synthesis of β-nitro alcohols from aldehydes and nitroalkanes is considered an efficient biocatalytic approach. However, only one S-selective HNL—Hevea brasiliensis (HbHNL)—exists that is appropriate for the synthesis of (S)-β-nitro alcohols from the corresponding aldehydes. Further, synthesis catalysed by HbHNL is limited by low specific activity and moderate yields. We have prepared a number of (S)-β-nitro alcohols, by kinetic resolution with the aid of an R-selective HNL from Arabidopsis thaliana (AtHNL). Optimization of the reaction conditions for AtHNL-catalysed stereoselective C?C bond cleavage of racemic 2-nitro-1-phenylethanol (NPE) produced (S)-NPE (together with benzaldehyde and nitromethane, largely from the R enantiomer) in up to 99 % ee and with 47 % conversion. This is the fastest HNL-catalysed route known so far for the synthesis of a series of (S)-β-nitro alcohols. This approach widens the application of AtHNL for the synthesis not only of (R)- but also of (S)-β-nitro alcohols from the appropriate substrates. Without the need for the discovery of a new enzyme, but rather by use of a retro-Henry approach, it was used to generate a number of (S)-β-nitro alcohols by taking advantage of the substrate selectivity of AtHNL.
Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions
Li, Zhi-Huai,Zhou, Zhi-Ming,Hao, Xiao-Yan,Zhang, Jun,Dong, Xiao,Liu, Ying-Qiang,Sun, Wen-Wen,Cao, Dan
experimental part, p. 28 - 34 (2012/07/01)
New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc)2· H2O were applied to the asymmetric Henry reaction using various aldehydes and CH3NO2/su
Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine-copper(II) complex
Selvakumar, Sermadurai,Sivasankaran, Dhanasekaran,Singh, Vinod K.
supporting information; experimental part, p. 3156 - 3162 (2011/02/25)
A copper(II) complex of C2-symmetric diamine has been proved to be an efficient catalyst for the enantioselective Henry reaction between nitroalkanes and various aldehydes to provide β-hydroxy nitroalkanes in high yields (up to 97%), moderate diastereoselectivities (up to 71:29) and excellent enantiomeric excesses (up to 96%). The chiral nitroaldol adduct obtained has been further converted into chiral aziridine in few steps.
