Lang Mylène, Tardieu Damien, Pousse Benoit, Compain Philippe, Kern Nicolas
Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France.
Chem Commun (Camb). 2024 Mar 14;60(23):3154-3157. doi: 10.1039/d3cc06249j.
Access to ,-glycosyl amino acids as a novel class of glycomimetics is reported by means of radical generation, intermolecular addition and stereoselective reduction a metal-induced hydrogen atom transfer (MHAT) sequence. The 'matched' coupling of -D-glycals with an enantiopure dehydroalanine bearing a ()-configured benzyl oxazolidinone enables a singular case of two-fold diastereocontrol under iron catalysis. In the common -D-glucal series, the nature of the C-2 substituent was found to play a key role from both reactivity and stereocontrol aspects.
通过自由基生成、分子间加成和立体选择性还原（一种金属诱导的氢原子转移（MHAT）序列），报道了获得作为一类新型糖模拟物的α-糖基氨基酸的方法。α-D-甘醇与带有(S)-构型苄基恶唑烷酮的对映体纯脱氢丙氨酸的“匹配”偶联，在铁催化下实现了罕见的双重非对映控制情况。在常见的α-D-葡萄糖系列中，发现C-2取代基的性质从反应性和立体控制方面都起着关键作用。
