132098-58-9Relevant articles and documents
Chiral alpha-amido aldehyde and preparation method thereof
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, (2020/12/29)
The invention relates to chiral alpha-amido aldehyde and a preparation method thereof. The method comprises the following steps that alpha-dehydroamido aldehyde shown in the following general formula(1) and hydrogen carry out a reduction reaction in an organic solvent under the catalytic action of a diphosphine-rhodium complex, and a chiral alpha-amido aldehyde compound shown in the following general formula (2) is obtained. The synthetic route adopts an asymmetric catalytic hydrogenation method, the process is simple, efficient and green, and the method is very suitable for industrial mass production. The product chiral amido aldehyde can be further derived into a chiral ligand and a chiral drug intermediate.
Chemo- and Enantioselective Hydrogenation of α-Formyl Enamides: An Efficient Access to Chiral α-Amido Aldehydes
Zhang, Jian,Jia, Jia,Zeng, Xincheng,Wang, Yuanhao,Zhang, Zhenfeng,Gridnev, Ilya D.,Zhang, Wanbin
, p. 11505 - 11512 (2019/07/17)
In order to effectively synthesize chiral α-amino aldehydes, which have a wide range of potential applications in organic synthesis and medicinal chemistry, a highly chemo- and enantioselective hydrogenation of α-formyl enamides has been developed, catalyzed by a rhodium complex of a P-stereogenic bisphosphine ligand. Under different hydrogen pressures, the chiral α-amido aldehydes and β-amido alcohols were obtained in high yields (97–99 %) and with excellent chemo- and enantioselectivities (up to >99.9 % ee). The hydrogenation can be carried out on a gram scale and with a high substrate/catalyst ratio (up to 20 000 S/C), and the hydrogenated products were further converted into several important chiral products. Computations of the catalytic cycle gave a clear description for the R/S pathways, provided a reasonable explanation for the enantioselectivity, and revealed several other specific features.
Bis(oxazoline)titanium complexes as chiral catalysts for enantioselective hydrosilylation of ketones - A combined experimental and theoretical investigation
Bandini, Marco,Bernardi, Fernando,Bottoni, Andrea,Cozzi, Pier Giorgio,Miscione, Gian Pietro,Umani-Ronchi, Achille
, p. 2972 - 2984 (2007/10/03)
A combined experimental and theoretical investigation has been carried out on a new catalytic system, based on bis-(oxazoline) (BOX) complexes of titanium. These catalytic species are able to reduce aromatic ketones with good enantiomeric excesses and satisfactory yields. The experimental and the computational (DFT) evidence has provided useful information on the nature of the active catalytic species and on the mechanism of the reaction. The most likely reaction path involves a TiIV catalytic species. This result agrees with experimentally obtained evidence that seems to rule out the presence of TiIII species. The analysis of the structure of the transition state corresponding to the reduction process (the addition of the hydride to the carbonyl system), provides an interesting insight on the enantioselectivity that characterizes this reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
