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(Polyfluoro)silane-mediated generation of azomethine ylides from imines and their cycloaddition leading to N-heterocycles

✍ Scribed by Mitsuo Komatsu; Hirofumi Okada; Seiji Yokoi; Satoshi Minakata

Book ID: 104252964
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 154 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00011-x

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✦ Synopsis

The novel generation and cycloaddition of azomethine ylides from an a-(trimethylsilyl)imine using (polyfluoro)silanes is described. The method was successfully applied to an efficient one-pot process. Namely, an azaallyl anion, generated by abstraction of the hydrogen a to an imino nitrogen, was treated with a di-or trifluorosilane to give an azomethine ylide intermediate below room temperature. The generated 1,3-dipole was smoothly trapped with dipolarophiles to afford nitrogen-containing five-membered heterocycles in good yields.

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## Abstract For Abstract see ChemInform Abstract in Full Text.