Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed <i>syn</i>-Selective Direct Aldol Reaction of Schiff Bases of Glycine <i>o</i>-Nitroanilide
作者:Silvia Vera、Ana Vázquez、Ricardo Rodriguez、Sandra del Pozo、Iñaki Urruzuno、Abel de Cózar、Antonia Mielgo、Claudio Palomo
DOI:10.1021/acs.joc.1c00406
日期:2021.6.4
Here we report the highly enantio- and syn-selective synthesis of β-hydroxy α-amino acids from glycine imine derivatives under Brønsted base (BB) catalysis. The key of this approach is the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity
在这里,我们报告了在 Brønsted 碱 (BB) 催化下从甘氨酸亚胺衍生物合成 β-羟基 α-氨基酸的高度对映选择性和顺选择性合成。该方法的关键是使用二苯甲酮衍生的甘氨酸邻硝基苯胺亚胺作为亲核试剂,其中邻硝基苯胺框架提供了一个有效的氢键平台,可解释亲核试剂的反应性和非对映选择性。