- 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 β-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.