Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde. Issue 8 (17th May 2017)

• Record Type: Journal Article
• Authors: Liu, Feng; Tian, Jiaxin; Liu, Yong; Tao, Chuangan; Zhu, Hao; Zhang, Aina; Xu, Dongfang; Zhao, Baoguo
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 8(2017)
• Page Start: 1586
• Page End: 1589
• Publication Date: 2017-05-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00846a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Decarboxylative Umpolung converts enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde group with excellent regio- and diastereoselectivities. Abstract : An interesting Umpolung strategy to generate β-carbanion equivalents from a conjugated enal has been developed. The enal group of compounds7 was chemospecifically converted to a delocalized carbanion by decarboxylation of the in situ formed imine between the enal and 2, 2-diphenylglycine (2 ), which then underwent nucleophilic addition at the β position of the enal to an intramolecular aldehyde group to give cyclized products8 in 54–93% yields.