Ring Opening of Donor-Acceptor Cyclopropanes with Acyclic 1,3-Diketones for the Synthesis of 1,6-Dicarbonyl Compounds

被引：13

作者：

Zhang, Dongxin ^{[1
]}

Cai, Hu ^{[1
]}

Chen, Yan ^{[1
]}

Yin, Lei ^{[1
]}

Zhong, Junchao ^{[1
]}

Zhang, Ying ^{[1
]}

Zhang, Qian-Feng ^{[1
]}

机构：

[1] Anhui Univ Technol, Inst Mol Engn & Appl Chem, Maanshan 243002, Anhui, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 21期

关键词：

D O I：

10.1021/acs.joc.0c02290

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,6-Dicarbonyl compounds, representing the formal addi-tion products of the a-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.

引用

页码：14262 / 14270

页数：9

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