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Ring Opening of Donor-Acceptor Cyclopropanes with Acyclic 1,3-Diketones for the Synthesis of 1,6-Dicarbonyl Compounds. 2020
Dongxin Zhang, and
Hu Cai, and
Yan Chen, and
Lei Yin, and
Junchao Zhong, and
Ying Zhang, and
Qian-Feng Zhang
Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, No. 59 Hudong Road, Ma'anshan, Anhui 243002, China.
1,6-Dicarbonyl compounds, representing the formal addition products of the α-position of acetophenone derivatives to donor-acceptor cyclopropanes, were synthesized in two steps via first ring opening of donor-acceptor cyclopropanes with acyclic 1,3-diketones followed by DBU catalyzed retro-Claisen-type C-C bond cleavage reactions. In the first step, acyclic 1,3-diketones selectively worked as C-nucleophiles to add to donor-acceptor cyclopropanes. In the second step, the alkyl ketone part of the ring-opening products resulting from unsymmetrical 1,3-diketones was selectively cleaved in the presence of DBU in methanol.
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