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Novel generation and cycloaddition of N-silylated azomethine ylides from α-silylimidates and trifluorosilane

✍ Scribed by Ken-Ichi Washizuka; Satoshi Minakata; Ilhyong Ryu; Mitsuo Komatsu

Book ID
104209685
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
458 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The Generation of N-silylated azomethine ylides was achieved by the reaction of asilylimidates and trifluorophenylsilane. The generated azomethine ylides can b¢ regarded as synthetic equivalents of nitrile ylides since they have an alkoxy group which may serve as a leaving group. Cycloaddition with acetylenic or olefinic dipolarophiles proceeded smoothly to give pyrrole or pyrroline derivatives in good to excellent yields, For example, ct-silylimidate I was treated with 1.2 equiv oftrifluorophenylsilane in the presence of I equiv of dimethyl aeetylenedicarboxylate to give pyrrole 2 in 97% yield. Furthermore, when starting with a secondary ot-silylamide, the one-pot synthesis ofN-unsubstituted azomethine ylides could be achieved by the successive treatment with alkylation and desilylation agents.

📜 SIMILAR VOLUMES

ChemInform Abstract: Novel Generation an
ChemInform Abstract: Novel Generation and Cycloaddition of N-Silylated Azomethine Ylides from α-Silylimidates and Trifluorosilane.
✍ Ken-Ichi Washizuka; Satoshi Minakata; Ilhyong Ryu; Mitsuo Komatsu 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Novel generation of azomethine ylide fro
Novel generation of azomethine ylide from N-(α-silylbenzyl)amide by silicon shift: an equivalent of nitrile ylide
✍ Mitsuru Ohno; Mitsuo Komatsu; Hiroyuki Miyata; Yoshiki Ohshiro 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 262 KB

Azomethine ylides were generated from N-(a-silylbenzyl)amides by thermal silicon shift to the oxygen and trapped with dipolarophiles to give the same products as those from the corresponding nitrile ylides via elimination of silanol.

(Polyfluoro)silane-mediated generation o
(Polyfluoro)silane-mediated generation of azomethine ylides from imines and their cycloaddition leading to N-heterocycles
✍ Mitsuo Komatsu; Hirofumi Okada; Seiji Yokoi; Satoshi Minakata 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 154 KB

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 tre