Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences, Urumqi 830011, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
J Org Chem. 2021 Feb 5;86(3):3049-3058. doi: 10.1021/acs.joc.0c02583. Epub 2021 Jan 28.
A series of α-mercapto-β-amino acid derivatives were synthesized diastereoselectively in good yields through the aza-enolization of α-sulfanyl --butanesulfinylimidates, followed by their nucleophilic addition to -tosyl imines via a Mannich-type reaction. The resulting derivatives bearing a β-sulfonylamino sulfide moiety participated in further inter- and intramolecular transformations involving episulfonium ion intermediates generated through neighboring-group participation.
一系列α-巯基-β-氨基酸衍生物通过α-硫代--丁烷亚磺酰基异吲哚啉的氮杂烯醇化反应立体选择性地以高产率合成，然后通过曼尼希型反应亲核加成到对甲苯磺酰亚胺。所得的带有β-磺酰氨基硫醚部分的衍生物参与了进一步的分子间和分子内转化，涉及通过邻基参与生成的环锍离子中间体。
