Reeve Philip A P, Grabowska Urszula, Oden Lourdes Salvador, Wiktelius Daniel, Wångsell Fredrik, Jackson Richard F W
Department of Chemistry, The University of Sheffield, Dainton Building, Sheffield S3 7HF, U.K.
Medivir AB, P.O. Box 1086, SE-141 22 Huddinge, Sweden.
ACS Omega. 2019 Jun 21;4(6):10854-10865. doi: 10.1021/acsomega.9b01509. eCollection 2019 Jun 30.
A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN allowed the preparation of side-chain azido-substituted amino acids (five examples), which upon catalytic hydrogenation gave the corresponding amines, isolated as lactams (four examples). Radical hydration of the unsaturated side chains leading to side-chain-hydroxylated protected amino acids has also been demonstrated.
通过用Fe(III)/NaBH和Selectfluor的组合处理含有不饱和侧链的保护氨基酸，制备了一系列对映体纯的保护侧链氟化氨基酸（13个实例）。用NaN取代Selectfluor对条件进行改性，从而制备了侧链叠氮基取代的氨基酸（5个实例），其经催化氢化得到相应的胺，以内酰胺形式分离出来（4个实例）。还证明了不饱和侧链的自由基水合反应可生成侧链羟基化的保护氨基酸。
