Zirconocene-Mediated Highly Regio- and Stereoselective Synthesis of Multisubstituted Olefins Starting from 1-Alkynylboronates
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- 作者：Yasushi Nishihara ; Mitsuru Miyasaka ; Masanori Okamoto ; Hideki Takahashi ; Eiji Inoue ; Kenki Tanemura ; Kentaro Takagi
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：October 24, 2007
- 年：2007
- 卷：129
- 期：42
- 页码：12634 - 12635
- 全文大小：63K
- 年卷期：v.129,no.42(October 24, 2007)
- ISSN：1520-5126
文摘
Multisubstituted olefins are efficiently prepared by the zirconocene-mediated regio- and stereoselective coupling between 1-alkynylboronates and ethylene, followed by sequential transformation in moderate to high yields. The proper combination of substrates and reaction conditions is important for high yields. The synthesis of various tetrasubstituted alkenes in a regio- and stereocontrolled manner is described. This methodology has been applied to the synthesis of (Z)-tamoxifen in a concise, regio- and stereoselective manner. This multicomponent coupling strategy involves the characteristics of 1-alkynylboronates toward high selectivities followed by palladium(0)-mediated cross-coupling with aryl halides.