Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
Angew Chem Int Ed Engl. 2016 Jun 13;55(25):7261-4. doi: 10.1002/anie.201602689. Epub 2016 May 11.
The increasing awareness of the importance of amide atropisomers prompts the development of novel strategies for their selective preparation. Described herein is a method for the enantioselective synthesis of atropisomeric aromatic amides by an amine-catalyzed arene-forming aldol condensation. The high reactivity of the glyoxylic amide substrates enables a remarkably efficient construction of a new aromatic ring, which proceeds within minutes at ambient temperature to afford products with excellent stereoselectivity. The high rotational barriers of the reduced products highlight the utility of this stable, spatially organized chiral scaffold.
酰胺对映异构体重要性的认识不断提高，促使人们开发出选择性制备它们的新策略。本文描述了一种通过胺催化的芳构化Aldol 缩合反应对映选择性合成对映异构芳香酰胺的方法。糖醛酰胺底物的高反应性使得非常有效地构建新的芳环成为可能，该反应在环境温度下几分钟内即可完成，产物具有优异的立体选择性。还原产物的高旋转势垒突出了这种稳定的、空间组织良好的手性支架的实用性。
