Catalytic Route to the Synthesis of Optically Active β,β-Difluoroglutamic Acid and β,β-Difluoroproline Derivatives
Catalytic Route to the Synthesis of Optically Active β,β-Difluoroglutamic Acid and β,β-Difluoroproline Derivatives
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DOI：
10.1021/jo049789c
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发表时间：
2004-06
影响因子：
3.6
通讯作者：
A. Suzuki;Masayuki Mae;H. Amii;K. Uneyama
中科院分区：
文献类型：
--
作者：
A. Suzuki;Masayuki Mae;H. Amii;K. Uneyama
以Mg（0）为催化剂，α-三氟甲基亚氨基酯为原料，经脱氟反应合成了β，β-二氟代氨基酸衍生物。二氟烯胺的溴化以良好的产率得到溴二氟甲基亚氨基酯。Pd催化的溴二氟甲基亚氨基酯的不对称氢化和随后的转化提供了光学活性的β，β-二氟谷氨酸和β，β-二氟脯氨酸衍生物。
β,β-Difluorinated amino acid derivatives were synthesized via Mg(0)-promoted defluorination of α-trifluoromethyl iminoester. Bromination of the difluoroenamine afforded the bromodifluoromethyl iminoester in good yield. Pd-catalyzed asymmetric hydrogenation of the bromodifluoromethyl iminoester and the subsequent transformations provided optically active β,β-difluoroglutamic acid and β,β-difluoroproline derivatives.