1590431-64-3Relevant academic research and scientific papers
General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors
Jang, Yujin,Lindsay, Vincent N. G.,Poteat, Christopher M.,Rivera, Roger Machín
supporting information, (2020/09/02)
The addition of organometallic reagents to ketones constitutes one of the most straightforward synthetic approaches to tertiary alcohols. However, due to the absence of a well-behaved class of cyclopropanone surrogates accessible in enantioenriched form, such a trivial synthetic disconnection has received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we report a simple and high-yielding synthesis of 1-substituted cyclopropanols via the addition of diverse organometallic reagents to 1-phenylsulfonylcyclopropanols, acting here as in situ precursors of the corresponding cyclopropanones. The transformation is shown to be amenable to sp-, sp2-, or sp3-hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions and the formation of optically active cyclopropanols.
Method for preparing 4-acetylenic ketone/ester compound and application thereof
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Paragraph 0078-0081; 0103; 0104; 0105; 0107; 0113, (2020/06/20)
The invention relates to a method for preparing a 4-acetylenic ketone/ester compound and an application thereof, and particularly provides a preparation method of a copper-mediated 4-acetylenic ketone/ester compound. The process is mild in reaction conditions and good in yield, and the compound has strong functional group tolerance and good compatibility.
Copper(II)-Mediated Ring Opening/Alkynylation of Tertiary Cyclopropanols by Using Nonmodified Terminal Alkynes
Cheng, Bu-Qing,Zhang, Si-Xuan,Cui, Yan-Ying,Chu, Xue-Qiang,Rao, Weidong,Xu, Haiyan,Han, Guo-Zhi,Shen, Zhi-Liang
supporting information, p. 5456 - 5461 (2020/07/14)
The copper(II)-mediated ring opening/alkynylation of cyclopropanol by employing inexpensive and commercially available terminal alkyne is developed. The reactions proceeded efficiently to afford synthetically useful alk-4-yn-1-ones in moderate to good yie
K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes to Form Pyridols
Wang, Shun,Guo, Yong-Qiang,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 1574 - 1577 (2017/04/13)
A novel K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.
Silver-Promoted Oxidative Ring Opening/Alkynylation of Cyclopropanols: Facile Synthesis of 4-Yn-1-ones
Wang, Cheng-Yong,Song, Ren-Jie,Xie, Ye-Xiang,Li, Jin-Heng
, p. 223 - 230 (2016/01/15)
A new silver-promoted oxidative ring opening/alkynylation of cyclopropanols with ethynylbenziodoxolones (EBX) is described. This method enables the formation of alkylated alkynes via a sequence of ring opening and alkynylation. Control experiments support
Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes
Zheng, Hongchao,Felix, Ryan J.,Gagne, Michel R.
, p. 2272 - 2275 (2014/05/06)
An enantioselective ring-expanding cycloisomerization of 1,5-enynes bearing a cyclopropylidene moiety has been developed. This methodology provides a new approach to bicyclo[4.2.0]octanes, a structural motif present in many biologically active natural products.
