Stereoselective functionalization of 1-alkoxy-2-(phenylethynyl)cyclopropanes via lithiation and subsequent reactions with electrophilic reagents
- 作者: Gvozdev V.1, Shavrin K.1, Ageshina A.2, Nefedov O.1
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隶属关系:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Higher Chemical College, Russian Academy of Sciences
- 期: 卷 66, 编号 5 (2017)
- 页面: 862-866
- 栏目: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240562
- DOI: https://doi.org/10.1007/s11172-017-1819-3
- ID: 240562
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详细
trans-1-Alkoxy-2-(phenylethynyl)cyclopropanes undergo lithiation at the hydrogen atom in the α-position to the triple bond on treatment with BuLi in THF at–(65—70) °C. The resulting organolithium derivatives react with acetaldehyde, acetone, dimethyl disulfide, and methyl chloroformate giving the corresponding alcohols, sulfides, and esters with the yields up to 69% with complete retention of cyclopropane ring stereoconfiguration. The obtained methyl 3-alkoxy-2,2-dimethyl-1-(phenylethynyl)cyclopropanecarboxylates and the corre-sponding acid readily undergo ring opening with addition of water molecule or HCl.
作者简介
V. Gvozdev
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
编辑信件的主要联系方式.
Email: vgvozdev2006@yandex.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991
K. Shavrin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: vgvozdev2006@yandex.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991
A. Ageshina
Higher Chemical College, Russian Academy of Sciences
Email: vgvozdev2006@yandex.ru
俄罗斯联邦, 9 Miusskaya pl., Moscow, 125047
O. Nefedov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: vgvozdev2006@yandex.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991