134936-19-9Relevant academic research and scientific papers
Highly Enantioselective Synthesis of syn-β-Hydroxy α-Dibenzylamino Esters via DKR Asymmetric Transfer Hydrogenation and Gram-Scale Preparation of Droxidopa
Sun, Guodong,Zhou, Zihong,Luo, Zhonghua,Wang, Hailong,Chen, Lei,Xu, Yongbo,Li, Shun,Jian, Weilin,Zeng, Jiebin,Hu, Benquan,Han, Xiaodong,Lin, Yicao,Wang, Zhongqing
supporting information, p. 4339 - 4342 (2017/08/23)
A highly efficient preparation of enantiomerically pure syn aryl β-hydroxy α-dibenzylamino esters is reported. The outcome was achieved via dynamic kinetic resolution and asymmetric transfer hydrogenation of aryl α-dibenzylamino β-keto esters. The desired products were obtained in high yields (up to 98%) with excellent diastereoselectivity (>20:1 dr) and enantioselectivity (up to >99% ee). Furthermore, this method was applied for the gram-scale preparation of droxidopa.
Applications of aziridinium ions. Selective syntheses of α,β-diamino esters, α-sulfanyl-β-amino esters, β-lactams, and 1,5-benzodiazepin-2-one
Chuang, Tsung-Hsun,Sharpless, K. Barry
, p. 3555 - 3557 (2007/10/03)
(matrix presented) A variety of nucleophiles, including amines, thiolates, and alkoxides, were employed to open the aziridinium ions Az. The latter are opened stereospecifically and regioselectively at the C-3 position by a wide range of amines, and thiol
Synthesis of serine analogues to be used as modified phospho acceptor sites in substrates of protein kinase C
Broxterman, H. J. G.,Liskamp, R. M. J.
, p. 46 - 52 (2007/10/02)
Serine and threonine analogues (compounds 2-6) are readily accessible by reaction of the anion of N,N-dibenzylglycine ethyl ester (1) with an appropriate carbonyl compound.These analogues will be incorporated into Protein Kinase C (PKC) substrates.The serine aldehyde derivative 7 was used for the preparation of the corresponding diethyl acetal 9.This compound was the starting material in the synthesis of the suicide precursor 8, featuring a reductive amination leading to 12 and a Lewis-acid-catalysed cyclization giving 8.
