Enantioselective direct vinylogous Michael addition for constructing enantioenriched γ, γ-dialkyl substituted butyrolactams and octahydroindoles. Issue 12 (7th March 2022)

• Record Type: Journal Article
• Authors: Yan, Jiahang; Zhang, Wenting; He, Qiaoqiao; Hou, Jun; Zeng, Hongxin; Wei, Hongbo; Xie, Weiqing
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 12(2022)
• Page Start: 2387
• Page End: 2391
• Publication Date: 2022-03-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00112h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A nickel(ii )/chiral N, N ′-dioxide catalyzed asymmetric direct vinylogous Michael addition of unsaturated butyrolactams enables synthesizing enantioenriched γ, γ-dialkyl substituted butyrolactams and octahydroindoles. Abstract : A nickel(ii )-catalyzed asymmetric direct vinylogous Michael addition of γ-alkyl monosubstituted α, β-unsaturated butyrolactams to α, β-unsaturated carbonyl compounds has been disclosed, affording γ, γ-dialkyl substituted butyrolactams in good yields and satisfactory enantioselectivities. A tandem catalytic asymmetric vinylogous Michael addition/intramolecular Michael addition has also been developed based on this reaction, which enabled the construction of enantioenriched octahydroindoles with three consecutive stereogenic carbon centers.