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Ru(II)‐Pheox Catalyzed Highly Stereoselective Cyclopropanation of Allyl‐ and Vinylsilanes with Diazoesters and Their Synthetic Applications
Author(s) -
Otog Nansalmaa,
Inoue Hayato,
Trinh Doan Thi Thuy,
Batgerel Zolzaya,
Langendorf Niklas Maximilian,
Fujisawa Ikuhide,
Iwasa Seiji
Publication year - 2021
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001427
Subject(s) - cyclopropanation , stereoselectivity , chemistry , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry
Abstract The stereoselective synthesis of optically active cyclopropylsilanes from various allyl‐ and vinylsilanes with functionalized diazoesters was achieved in excellent yields (up to 99 %) and diastereo‐ (up to >99 : 1 d.r.) and enantioselectivities (up to 99 % ee) in the presence of Ru(II)‐Pheox catalysts. Among a series of Ru(II)‐Pheox catalysts, p ‐MeO−Ru(II)‐Pheox was determined to be the best catalyst for cyclopropanation reactions of diazoesters with various allylsilanes. Also, methyl(diazoacetoxy)acetate afforded in significantly enhanced yields, diastereoselectivities, and enantioselectivities. The cyclopropanation reactions with vinylsilanes with methyl (diazoacetoxy)acetate proceeded with excellent diastereoselectivities (>99 : 1 d.r.). Moreover, cyclopropylsilane derivatives could be successfully transformed into beneficial building blocks for the synthesis of bioactive compounds, including an anti‐HIV drug and Imatinib‐7.