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제125회 대한화학회 학술발표회 및 총회 Construction of 9-Membered 1,4-Oxazonine via Synergistic Rh(II)/Pd(0) Dual Catalytic [6+3] Dipolar Cycloaddition Reaction

2020년 2월 4일 11시 16분 37초
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Organic Chemistry
저자 및
Kyu Ree Lee, Subin Ahn, Sang-gi Lee1,*
Department of Chemistry and Nanoscience, Ewha Womans University, Korea
1Chemistry Department of Nano-Science, Ewha Womans University, Korea

Medium-sized heterocycles are ubiquitous in biologically active natural products. Although transition metal catalyzed synthesis of 4- to 7-membered heterocyclic compounds is well-established, formation of medium sized cyclic molecules which are larger than 7-membered rings still has been challenging realm of organic synthesis[1]. During our ongoing study on cooperative dual catalysis,[2] we envisioned that the 9-membered 1,4-oxazonine heterocyclic compounds could be constructed through the synergistic Rh(II)/Pd(0) dual catalytic [6+3] dipolar cycloaddition reaction between the catalytically generated reactive intermediates, i.e., 1,3-dipole equivalent alpha-imino Rh-carbenoid formed from 1,2,3-triazoles 1 and 1,6-dipole equivalent zwitterionic alkoxy pi-allyl Pd(II)-complex formed from 4-vinyl-1,3-dioxan-2-one 2 (Scheme 1). Reference [1] (a) Yet, L. Chem. Rev. 2000, 100, 2963. (b) Vo, C.-V. T.; Luescher, M. U.; Bode, J. W. Nat. Chem. 2014, 6, 310. [2] (a) Chen, Z.-S.; Huang, L.-Z.; Jeon, H. J.; Xuan, Z.; Lee, S.-g. ACS Catal. 2016, 6, 4914. (b) Huang, L.-Z.; Xuan, Z.; Jeon, H. J.; Du, Z.-T.; Kim, J. H.; Lee, S.-g. ACS Catal. 2018, 8, 7340.