DBU‐Catalyzed Regioselective α‐Alkylation of Enones Using the Vinylogous Strategy. Issue 7 (26th May 2021)

• Record Type: Journal Article
• Authors: Tian, Yawei; Shang, Yaping; Su, Weiping
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 7(2021)
• Page Start: 1718
• Page End: 1721
• Publication Date: 2021-05-26
• Subjects: organocatalysis -- enones -- α-alkylation -- dienolate -- regioselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100293
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A convenient and atom‐economic transformation of enones with electron‐deficient alkenes under mild conditions has been developed using DBU as a catalyst. This method utilizes vinylogous strategy to form dienolate intermediates, which provides a new approach for the regioselective α‐alkylation of enones. This protocol exhibits a broad range of substrate scope and good functional group compatibility. Moreover, it enabled the formation of unexpected cyclic 1, 5‐diketone by employing phenyl acrylate as Michael acceptor to construct all‐carbon quaternary centers at γ‐position of enones. Overall, this synthetic method establishes a new route from readily available enones to valuable 1, 5‐dicarbonyl compounds. Abstract : We report herein a convenient α‐alkylation of enones with electron‐deficient alkenes under mild conditions. This protocol offers a direct access to 1, 5‐dicarbonyl compounds in synthetically useful yields using vinylogous strategy via dienolate intermediates.