二苯基脯氨醇硅醚催化α-三氟甲基硫酯与α,β-不饱和醛的不对称迈克尔反应
Asymmetric Michael Reaction of α-CF Thioester and α,β-Unsaturated Aldehyde Catalyzed by Diphenylprolinol Silyl Ether.
作者信息
Hayashi Yujiro, Yamada Tomoaki, Sato Misaki, Watanabe Shoya, Kwon Eunsang, Iwasaki Kotaro, Umemiya Shigenobu
机构信息
Department of Chemistry, Graduate School of Science , Tohoku University , 6-3 Aramaki Aza-Aoba , Aoba-ku, Sendai , Miyagi 980-8578 , Japan.
Research and Analytical Center for Giant Molecules, Graduate School of Science , Tohoku University , 6-3 Aramaki Aza-Aoba , Aoba-ku, Sendai , Miyagi 980-8578 , Japan.
出版信息
Org Lett. 2019 Jul 5;21(13):5183-5186. doi: 10.1021/acs.orglett.9b01774. Epub 2019 Jun 18.
Asymmetric Michael reaction of α-CF thioester and α,β-unsaturated aldehyde is catalyzed by diphenylprolinol silyl ether to afford the trifluoromethyl substituted Michael product with excellent enantioselectivity. Although the Michael products were generated as a mixture of syn- and anti-isomers, they can be transformed to single isomers of other useful compounds, such as lactone, lactam, piperidine, dihydropyran containing trifluoromethyl groups, or fluoro substituents.
二苯基脯氨醇硅醚催化α-三氟甲基硫酯与α,β-不饱和醛的不对称迈克尔反应，以优异的对映选择性得到三氟甲基取代的迈克尔产物。虽然迈克尔产物以顺式和反式异构体的混合物形式生成，但它们可以转化为其他有用化合物的单一异构体，如含三氟甲基或氟取代基的内酯、内酰胺、哌啶、二氢吡喃。
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