Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate
Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate
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甘氨酸合成子与甲基丙烯酸甲酯的不对称迈克尔加成，由 TADDOLate 二钠介导
DOI：
10.1070/mc1997v007n04abeh000790
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发表时间：
1997
影响因子：
1.9
通讯作者：
A. A. Chesnokov
中科院分区：
文献类型：
--
作者：
Y. Belokon’;K. Kochetkov;T. D. Churkina;N. S. Ikonnikov;S. A. Orlova;V. Smirnov;A. A. Chesnokov
(4R,5R)-(TADDOL),3 的二钠盐可用作不对称迈克尔反应中的介体。甘氨酸合成子 1 与甲基丙烯酸甲酯 2 的 1,4-加成，由 3 (10-100 mol%) 介导，得到相应产物 4 的非对映异构体过量高达 65%，对映体纯度约为 15%。 28%； (2S,4R)-4-甲基谷氨酸(ee≥85%)6是以(2S,4R)-4(ee 28%)为原料，经重结晶、分解得到(2S,4R)-4-甲基谷氨酸(ee≥85%)6。
The disodium salt of (4R,5R)-(TADDOL),3, can be used as a mediator in the asymmetric Michael reactione.g. 1,4-addition of a glycine synthon 1 to methyl methacrylate 2, mediated by 3 (10-100 mol%), gives a diastereoisomeric excess of the corresponding product 4 up to 65% and an enantiomeric purity ca. 28%; (2S,4R)-4-methylglutamic acid (ee ≥ 85%), 6, was obtained starting from (2S,4R)-4 (ee 28%) through the recrystallization and decomposition of the latter.