251325-74-3Relevant academic research and scientific papers
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.
Asymmetric synthesis of β-amino alcohols and 1,2-diamines through DuPHOS-Rh catalysed hydrogenation
Burk, Mark J.,Johnson, Nicholas B.,Lee, Jeffrey R.
, p. 6685 - 6688 (2007/10/03)
A novel enantioselective synthesis of β-amino alcohols and 1,2-diamines is reported which incorporates the first description of the asymmetric hydrogenation of dehydro-β-amino alcohols and dehydro-α-amino aldoximes.
