无保护α-氨基酸合成多手性中心2(5H)-呋喃酮化合物

Synthesis of 5H-Funan-2-ones with Multiple Chiral Centers Directly from Unprotected α-Amino Acids

以无保护的α-氨基酸为亲核试剂,与不同的手性(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮进行串联的迈克尔加成-消除反应,合成了15个新的光学活性2(5H)-呋喃酮衍生物.利用旋光度,UV-Vis,IR,1HNMR,13CNMR,MS,元素分析和X射线单晶衍射等表征方法,确定了新的多手性中心2(5H)-呋喃酮化合物的化学结构和绝对构型.

Five unprotected α-amino acids, serving as nucleophiles, were reacted with different （5S）-5-alkoxy-3,4-dihalo-5H-furan-2-ones via tandem Michael addition-elimination to give 15 new optically active 5H-furan-2-one derivatives. The chemical structures and absolute configurations of these compounds with multiple chiral centers were confirmed via rotation, UV-Vis, IR, 1H NMR, 13C NMR, MS, elemental analy-sis and X-ray single crystal diffraction.