著者
福留 裕樹 畠山 琢次 原 賢二 中村 正治 中村 栄一
出版者
基礎有機化学会(基礎有機化学連合討論会)
雑誌
基礎有機化学討論会要旨集(基礎有機化学連合討論会予稿集)
巻号頁・発行日
vol.16, pp.1103, 2002

Development of the stereocontrolled carbon-carbon bond formation is one of the most important tasks in synthetic organic chemistry. We have reported that a zincated hydrazone, which is a synthetic equivalent and an isoelectronic compound of a metal enolate, reacts with various vinyl metal compounds such as vinyl silane, vinyl stannane, and vinylmagnesium halide to form a new functionalized organometallics bearing two metals at the same carbon. We recently found that a vinyl boronate can also serve as the carbometalation acceptor and shows high reactivity toward organozinc reagents. Here we report an alkenyl boronate, which possesses a variety of substituent at the &beta;-carbon to boron, undergoes the addition of a zincated hydrazone in high yields with high diastereoselectivity. The zincated hydrazone derived from 2-methyl-3-pentanone hydrazone, thus, reacted with <I>trans-</i>hexenyl boronate to give a product in 92% yield with high diastereoselectivity (d.r. > 99:1). On the other hand, the reaction to the corresponding <I>cis-</i>isomer gave another diastereomer with a diastereoselectivity of 16:84, showing high stereospecificity of the carbozincation process.

言及状況

外部データベース (DOI)

Twitter (1 users, 2 posts, 0 favorites)

こんな論文どうですか? アルケニルホウ素化合物への亜鉛化ヒドラゾンの立体選択的付加反応(福留 裕樹ほか),2002 https://t.co/cgu59UAtgC Development of the stereocontrolled carbon…
こんな論文どうですか? アルケニルホウ素化合物への亜鉛化ヒドラゾンの立体選択的付加反応(福留 裕樹ほか),2002 https://t.co/cgu59UAtgC Development of the stereocontrolled carbon…

収集済み URL リスト