Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst
Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst
复制标题
使用二氨基亚甲基丙二腈有机催化剂将 α-氰酮不对称共轭加成到苯甲酰丙烯腈衍生物中
DOI：
10.1055/s-0040-1707285
复制
发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Miura Tsuyoshi
中科院分区：
文献类型：
--
作者：
Akutsu Hiroshi;Nakashima Kosuke;Kanetsuna Yuta;Kawada Masahiro;Hirashima Shin-ichi;Miura Tsuyoshi
采用二氨基亚甲基丙二腈（DMM）有机催化剂，有效地促进了α-氰基酮与苯甲酰基丙烯腈衍生物的不对称共轭加成反应.相应的1，5-二羰基化合物含有邻位的叔和季立体中心是通用的合成中间体，并获得了良好的产率和优良的对映选择性（高达96%ee）。本文首次报道了α-氰基酮与苯甲酰基丙烯腈的不对称共轭加成反应。此外，DMM有机催化剂可以回收和重复使用多达五次，而没有显着的损失，无论是催化活性或对映选择性。
A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.
α-氰酮的催化不对称共轭加成用于构建四元立构中心。
影响因子：
5.2
作者：
Yuji Kawato;Noriko Takahashi;N. Kumagai;M. Shibasaki
通讯作者：
M. Shibasaki