Zinc-Catalyzed Allenylations of Aldehydes and Ketones
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- 作者：Daniel R. Fandrick ; Jaideep Saha ; Keith R. Fandrick ; Sanjit Sanyal ; Junichi Ogikubo ; Heewon Lee ; Frank Roschangar ; Jinhua J. Song ; Chris H. Senanayake
- 刊名：Organic Letters
- 出版年：2011
- 出版时间：October 21, 2011
- 年：2011
- 卷：13
- 期：20
- 页码：5616-5619
- 全文大小：756K
- 年卷期：v.13,no.20(October 21, 2011)
- ISSN：1523-7052
文摘
The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc intermediate, the addition to the electrophile effectively competes with propargyl-allenyl zinc equilibration. The utility of the methodology was demonstrated by application to a rhodium-catalyzed [4 + 2] cycloaddition.