Cross-Metathesis Reactions as an Efficient Tool in the Synthesis of Fluorinated Cyclic β-Amino Acids
作者:Santos Fustero、María Sánchez-Roselló、José Luis Aceña、Begoña Fernández、Amparo Asensio、Juan F. Sanz-Cervera、Carlos del Pozo
DOI:10.1021/jo900296d
日期:2009.5.1
The synthesis of enantiomerically pure, cyclic, γ,γ-difluorinated β-amino acids with various ring sizes has been carried out with a cross-metathesis (CM) reaction being one of the key steps, followed by a Dieckmann-type condensation to bring about the cyclization. Subsequent catalytic hydrogenation under microwave irradiation with (−)-8-phenylmenthol as a chiral auxiliary led to the successful chemo-
进行了对映体纯的,环状,各种环尺寸的γ,γ-二氟β-氨基酸的合成,其中交叉复分解(CM)反应是关键步骤之一,然后进行Dieckmann型缩合反应关于环化。随后在微波辐射下,以(-)-8-苯基薄荷醇为手性助剂进行催化加氢,成功地完成了所生成的环状β-烯胺酯的化学和非对映选择性化学还原。为了确定关于选择性和反应性的最佳反应条件,还研究了与不同类型的氟化亚氨酰氯和不饱和酯的CM反应的效率和范围。