α-Arylation and Ring Expansion of Annulated Cyclobutanones: Stereoselective Synthesis of Functionalized Tetralones
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- 作者：Dr. Stanley Chang ; Dr. Michael Holmes ; Dr. Jeffrey Mowat ; Michael Meanwell and Prof. Robert Britton
- 刊名：Angewandte Chemie International Edition
- 出版年：2017
- 出版时间：January 16, 2017
- 年：2017
- 卷：56
- 期：3
- 页码：748-752
- 全文大小：1136K
- ISSN：1521-3773
文摘
α-Arylcyclobutanones display unique reactivity that makes them valuable synthetic intermediates and target molecules. We describe the preparation of α-aryl- and α-heteroarylcyclobutanones through a direct α-arylation reaction. Problematic fragmentations are avoided by the use of LiOtBu, which promotes a rapid but reversible self-aldol reaction that slowly releases the enolate required for α-arylation. We also demonstrate the ring expansion of α-arylcyclobutanones, a process that is highlighted in the stereoselective synthesis of 1-methoxy coniothyrinone D.