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Highly chemo- and enantioselective vinylogous aldol/cyclization cascade reaction to construct chiral 5,6-dihydropyran-2-ones
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-22 , DOI: 10.1016/j.tet.2018.05.011
Zhen-Guo Zhang , Jun-Hao Fu , Feng Sha , Xin-Yan Wu

An organocatalytic chemo- and enantioselective vinylogous aldol/cyclization cascade reaction between β,γ-unsaturated amides and β,γ-unsaturated α-keto esters was developed. With 5 mol% of chiral tertiary amine-thiourea catalyst C3, highly functionalized 5,6-dihydropyran-2-ones with a quaternary stereocenter were constructed in a straightforward manner with high yields (up to 99%) and excellent enantioselectivities (up to 98% ee).



中文翻译:

高度化学和对映选择性乙烯基醇醛/环化级联反应,以构建手性5,6-二氢吡喃-2-酮

开发了β,γ-不饱和酰胺与β,γ-不饱和α-酮酯之间的有机催化化学和对映选择性乙烯基醇醛/环化级联反应。用5 mol%的手性叔胺-硫脲催化剂C3,可以直接,高收率(高达99%)和出色的对映选择性(高达98)构建具有四级立体中心的高度官能化的5,6-二氢吡喃-2-酮。 %ee)。

更新日期:2018-05-22
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