Stereoselective functionalization of 1-alkoxy-2-(phenylethynyl)cyclopropanes via lithiation and subsequent reactions with electrophilic reagents
- Authors: Gvozdev V.D.1, Shavrin K.N.1, Ageshina A.A.2, Nefedov O.M.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Higher Chemical College, Russian Academy of Sciences
- Issue: Vol 66, No 5 (2017)
- Pages: 862-866
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240562
- DOI: https://doi.org/10.1007/s11172-017-1819-3
- ID: 240562
Cite item
Abstract
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.
About the authors
V. D. Gvozdev
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: vgvozdev2006@yandex.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
K. N. Shavrin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: vgvozdev2006@yandex.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. A. Ageshina
Higher Chemical College, Russian Academy of Sciences
Email: vgvozdev2006@yandex.ru
Russian Federation, 9 Miusskaya pl., Moscow, 125047
O. M. Nefedov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: vgvozdev2006@yandex.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991