Department of Organic Chemistry, Charles University, Hlavova 8, 12843, Prague, Czech Republic.
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 16610, Prague, Czech Republic.
Chemistry. 2018 Sep 12;24(51):13441-13445. doi: 10.1002/chem.201803677. Epub 2018 Aug 17.
The present study reports the organocatalytic enantioselective allylic amination of Morita-Baylis-Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Brønsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
本研究报告了在布朗斯台德酸存在下,手性伯胺高效催化的 Morita-Baylis-Hillman 氨基甲酸酯的对映选择性烯丙基胺化反应。手性烯丙基胺以高产率(高达 98%)和对映选择性(高达 97%ee)得到。该方法提供了一种有效且易于操作的途径来制备α-亚甲基-β-内酰胺,以及其他光学活性的β-内酰胺,如降胆固醇药物依泽替米贝。