异噁唑酮与氧化吲哚-3-氧基丙烯酸酯的多样化缝合：一种用于合成多种3/5-螺[呋喃-2,3'-吲哚]-2'-酮的单瓶螺环化方案
Diversified Stitching of Ynones with Oxindole-3-oxy acrylates: One-Flask Spiro-annulation Protocol toward Assorted 3/5-Spiro[furan-2,3'-indolin]-2'-ones.
作者信息
Sarma Manas Jyoti, Sudarshana K A, Pabbaraja Srihari, Mehta Goverdhan
机构信息
School of Chemistry, University of Hyderabad, Hyderabad 500046, India.
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
出版信息
J Org Chem. 2023 Aug 18;88(16):12131-12140. doi: 10.1021/acs.joc.3c01279. Epub 2023 Jul 28.
Spiroannulation of oxindole-3-oxy acrylates with ynones involving two overlapping, base differentiated cascades has been observed. Initial exposure of ynones and oxindole 3-oxy acrylates to KCO triggered a tandem Michael-Michael cascade to deliver a pair of spiroannulated diastereomers. Further exposure to LiHMDS led to deep restructuring through a second multistep cascade involving stereoselective recreation of the C3 quaternary center to furnish 3-spiro[furan-2,3'-indolin]-2'-ones with functional amplification and scrambling. This new scaffold can be directly accessed in a one-flask operation from ynones and oxindole-3-oxy acrylates.
已观察到3-氧化吲哚丙烯酸酯与炔酮的螺环化反应涉及两个重叠的、碱区分的串联反应。首先将炔酮和3-氧化吲哚丙烯酸酯暴露于碳酸钾引发串联迈克尔-迈克尔反应，生成一对螺环化非对映异构体。进一步暴露于二(三甲基硅基)氨基锂会导致深度重排，通过涉及C3季碳中心立体选择性重建的第二个多步串联反应，得到具有官能团放大和重排的3-螺[呋喃-2,3'-吲哚]-2'-酮。这种新的骨架可以通过炔酮和3-氧化吲哚丙烯酸酯在单瓶操作中直接获得。
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