Division of Organic Chemistry, National Chemical Laboratory , Dr. Homi Bhabha Road, Pune, India 411008.
Org Lett. 2014 Feb 7;16(3):648-51. doi: 10.1021/ol4037117. Epub 2014 Jan 17.
A highly regio- and diastereoselective TMSOTf promoted vinylogous Mannich reaction for the synthesis of chiral quaternary 3-aminooxindole butenolides from 2-silyloxy furans and chiral ketimines is described. The method is found to be very efficient and also provides a facile access to sterically challenging 3-aminooxindole butenolides bearing two quaternary centers in continuation. Further, the versatility of the method is demonstrated by the 1,4-addition of nucleophiles on the sterically congested butenolide substructure.
一种高区域和立体选择性的 TMSOTf 促进的 vinylogous Mannich 反应，用于从 2-硅氧基呋喃和手性亚胺合成手性季碳 3-氨基氧吲哚丁烯内酯，被描述。该方法被发现非常有效，并且还提供了一种易于获得具有两个季碳中心的空间位阻大的 3-氨基氧吲哚丁烯内酯的方法。此外，该方法的多功能性通过在空间拥挤的丁烯内酯亚结构上进行亲核 1,4-加成得到了证明。
