N-Heterocyclic carbene catalyzed chemo- and enantioselective cross-benzoin reaction of aldehydes with isatins. Issue 2 (28th November 2018)

• Record Type: Journal Article
• Authors: Xu, Jianfeng; Peng, Jingyi; He, Chonglong; Ren, Hongjun
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 2(2019)
• Page Start: 172
• Page End: 176
• Publication Date: 2018-11-28
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo01085d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A highly chemoselective N-heterocyclic carbene catalyzed intermolecular cross-benzoin reaction of aldehydes with isatins to afford enantioenriched 3-substituted-3-hydroxyoxindoles is described. Abstract : A highly chemoselective intermolecular cross-benzoin reaction of aldehydes with isatins enabled by asymmetric N-heterocyclic carbene (NHC) catalysis is described, and it provides 3-substituted-3-hydroxyoxindoles in moderate to good yields with moderate to excellent enantioselectivities. This reaction can be readily scaled up, the products could be straightforwardly reduced to the corresponding 1, 2-diols, and the trityl (Trt) protecting group could be easily removed without erosion of enantioselectivities.