1380403-08-6Relevant academic research and scientific papers
Concise synthesis of (-)-anisomycin
Li, Ji,Feng, Yan Hua,Li, Xin Bai,Han, Wei,Liu, Huan Qiu,Shao, Guo Guang
, p. 647 - 649 (2012)
The antibiotic (-)-anisomycin was synthesized starting from d-tyrosine using Sharpless asymmetric epoxidation as a key reaction followed by formation and hydrolysis of oxazoline set up all chiral center.
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.
