Asymmetric Cycloadditions of Acyclic Carbonyl Ylides with Aldehydes Catalyzed by a Chiral Binaphthyldiimine-Ni(II) Complex: Enantioselective Synthesis of 1,3-Dioxolanes and Mechanistic Studies by DFT Calculations
Yasunori Toda, Kayo Sato, Kensuke Sato, Kazuma Nagasaki, Hirotaka Nakajima, Ayaka Kikuchi, Kimiya Sukegawa and Hiroyuki Suga*
*Department of Materials Chemistry, Faculty of Engineering, Shinshu University 4-17-1 Wakasato, Nagano 380-8553, Japan,
Email: sugahio
shinshu-u.ac.jp
Y. Toda, K. Sato, K. Sato, K. Nagasaki, H. Nakajima, A. Kikuchi, K. Sukegawa, H. Suga, Org. Lett., 2022, 24, 4739-4744.
DOI: 10.1021/acs.orglett.2c01682
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Abstract
A chiral binaphthyldiimine-Ni(II) complex catalyzes an asymmetric 1,3-dipolar cycloaddition reactions between acyclic carbonyl ylides generated from donor-acceptor oxiranes and both aromatic and aliphatic aldehydes to provide cis-1,3-dioxolanes with high diastereo- and enantioselectivities.
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Key Words
ID: J54-Y2022
