环丙烷开环与非环状 1,3-二酮反应合成 1,6-二羰基化合物。
Ring Opening of Donor-Acceptor Cyclopropanes with Acyclic 1,3-Diketones for the Synthesis of 1,6-Dicarbonyl Compounds.
机构信息
Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, No. 59 Hudong Road, Ma'anshan, Anhui 243002, China.
出版信息
J Org Chem. 2020 Nov 6;85(21):14262-14270. doi: 10.1021/acs.joc.0c02290. Epub 2020 Oct 28.
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.
1,6-二羰基化合物是由苯乙酮衍生物的α-位与给体-受体环丙烷加成形成的加合物，可通过两步法合成：首先，无环 1,3-二酮与给体-受体环丙烷开环，然后在 DBU 催化的反-Claisen 型 C-C 键断裂反应中进行。在第一步中，无环 1,3-二酮作为 C-亲核试剂选择性地与给体-受体环丙烷加成。在第二步中，在甲醇中存在 DBU 时，不对称 1,3-二酮的开环产物中的烷基酮部分被选择性地裂解。
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