Synthesis, Table of Contents

Synthesis 2012; 44(23): 3623-3632
DOI: 10.1055/s-0032-1317507

paper

© Georg Thieme Verlag Stuttgart · New York

Coupling Reaction of Magnesium Alkylidene Carbenoids with α-Sulfonylallyllithiums: An Efficient Route to Multi-Substituted Vinylallenes

Tsutomu Kimura

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan

,

Gen Kobayashi

^bGraduate School of Chemical Sciences and Technology, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan Fax: +81(3)52614631 Email: tsatoh@rs.kagu.tus.ac.jp

,

Masashi Ishigaki

^bGraduate School of Chemical Sciences and Technology, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan Fax: +81(3)52614631 Email: tsatoh@rs.kagu.tus.ac.jp

,

Mio Inumaru

^bGraduate School of Chemical Sciences and Technology, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan Fax: +81(3)52614631 Email: tsatoh@rs.kagu.tus.ac.jp

,

Jo Sakurada

^bGraduate School of Chemical Sciences and Technology, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan Fax: +81(3)52614631 Email: tsatoh@rs.kagu.tus.ac.jp

,

Tsuyoshi Satoh*

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan

^bGraduate School of Chemical Sciences and Technology, Tokyo University of Science, 12 Ichigaya-funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan Fax: +81(3)52614631 Email: tsatoh@rs.kagu.tus.ac.jp

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Abstract

A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as α-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of α-sulfonylallyllithiums with magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield.

Key words

Key words

vinylallenes - magnesium alkylidene carbenoids - allyl sulfones - vinyl sulfones - 1-chlorovinyl p-tolyl sulfoxides - coupling

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Supplementary Material

Supplementary Material

Supporting Information