Synthesis, Table of Contents Synthesis 2021; 53(03): 527-537DOI: 10.1055/s-0040-1706469 paper t BuO2H/Cu(acac)2-Mediated Intramolecular Oxidative Lactonization of o-Allyl Arylaldehydes: Synthesis of 1-Oxoisochromans Meng-Yang Chang ∗ a Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100 Shin-Chuan 1st Rd., Kaohsiung 80708, Taiwan b Department of Medical Research, Kaohsiung Medical University Hospital, 100 Tzyou 1st Rd., Kaohsiung 80708, Taiwan Email: mychang@kmu.edu.tw , Kai-Xiang Lai a Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100 Shin-Chuan 1st Rd., Kaohsiung 80708, Taiwan , Kuan-Ting Chen a Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100 Shin-Chuan 1st Rd., Kaohsiung 80708, Taiwan› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract A concise route for the t BuO2H/Cu(acac)2-mediated synthesis of 1-oxoisochromans is described. This includes: (i) oxidation of oxygenated o-allyl arylaldehydes and (ii) sequential intramolecular lactonization of the resulting olefin-containing benzoic acids. A plausible mechanism is proposed and discussed. Key words Key words t BuO2H - Cu(acac)2 - 1-oxoisochromans - intramolecular oxidative annulation - o-allyl arylaldehydes Full Text References References 1 Katsuki T, Sharpless KB. J. Am. Chem. Soc. 1980; 102: 5974 2 Rossiter BE, Verhoeven TR, Sharpless KB. Tetrahedron Lett. 1979; 20: 4733 For Cu(II), see: 3a Zhu Y, Yan H, Lu L, Liu D, Rong G, Mao J. J. Org. Chem. 2013; 78: 9898 3b Yedage SL, Bhanage BM. Synthesis 2015; 47: 526 3c Route SK, Guin S, Ghara KK, Banerjee A, Patel BK. Org. Lett. 2012; 14: 3982 3d Han C, Yu M, Sun W, Yao Y. Synlett 2011; 2363 3e Bathini T, Rawat VS, Streedhar B. Synlett 2015; 26: 1348 3f Wang C, Zhangm J, Wang S, Fan J, Wang Z. Org. Lett. 2010; 12: 2338 3g Mahesh D, Sadhu P, Punniyamurthy T. J. Org. 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Tetrahedron 2013; 69: 2933 Supplementary Material Supplementary Material Supporting Information CIF File
