Access to Enantiopure Triarylmethanes and 1,1-Diarylalkanes by NHC-Catalyzed Acylative Desymmetrization

详细信息    查看全文

• 作者：Dr. Shenci Lu ; Dr. Xiaoxiao Song ; Si Bei Poh ; Dr. Hui Yang ; Prof. Ming Wah Wong and Prof. Yu Zhao
• 刊名：Chemistry - A European Journal
• 出版年：2017
• 出版时间：February 16, 2017
• 年：2017
• 卷：23
• 期：10
• 页码：2275-2281
• 全文大小：1663K
• ISSN：1521-3765

文摘

We present herein an unprecedented, efficient and enantioselective synthesis of triarylmethanes and 1,1-diarylalkanes through N-heterocyclic carbene-catalyzed acylative desymmetrization of bisphenols. This method utilizes readily available substrates, reagents and a simple procedure to deliver the valuable products in excellent enantiopurity. DFT calculations reveal that the selectivity is governed by the C−C bond cleavage step of the tetrahedral intermediate leading to the ester product. A transition state model featuring a combination of intramolecular hydrogen bond and steric effect is developed to explain the enantioselectivity.