5-取代呋喃-2(3H)-酮对α,β-不饱和-γ-内酰胺的不对称乙烯基迈克尔加成反应。
Asymmetric vinylogous Michael addition of 5-substituted-furan-2(3)-ones to an α,β-unsaturated-γ-lactam.
机构信息
Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
出版信息
Org Biomol Chem. 2020 Nov 4;18(42):8633-8637. doi: 10.1039/d0ob01750g.
The manuscript describes an utilization of 5-substituted-furan-2(3H)-ones as pronucleophiles in an asymmetric vinylogous Michael addition to an α,β-unsaturated-γ-lactam, thus leading to hybrid molecules possessing γ-lactam and butenolide structural motifs. The transformation utilizes two potentially vinylogous pronucleophiles and has been realized by simultaneous activation of both substrates by a bifunctional organocatalyst derived from a cinchona alkaloid. Reaction occurs in a highly enantio- and diastereoselective manner and the synthetic potential of the target products has been confirmed in stereoselective transformations.
该手稿描述了 5-取代呋喃-2(3H)-酮作为亲核试剂在不对称乙烯基迈克尔加成到α,β-不饱和-γ-内酰胺中的应用，从而得到了具有γ-内酰胺和丁烯内酯结构基序的杂化分子。该转化利用了两个潜在的乙烯基亲核试剂，并通过由金鸡纳生物碱衍生的双功能有机催化剂同时激活两个底物来实现。反应以高度对映选择性和非对映选择性的方式进行，目标产物的合成潜力已在立体选择性转化中得到证实。
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