Dutta Sourav, Porey Arka, Guin Joyram
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, India.
Chem Commun (Camb). 2023 May 9;59(38):5771-5774. doi: 10.1039/d3cc00489a.
Herein, we describe an effective strategy for enantioselective synthesis of oxindoles having a C3-quaternary stereocenter N-heterocyclic carbene (NHC) catalyzed desymmetrization of diols. The process is based on the catalytic asymmetric transfer acylation of primary alcohols using readily available aldehydes as an acylation agent. The reaction enables easy access to diversely functionalized C3-quaternary oxindoles with excellent enantioselectivity. The synthetic potential of the process is further demonstrated the preparation of the key intermediate for (-)-esermethole and (-)-physostigmine.
在此，我们描述了一种对映选择性合成具有C3-季碳立体中心的羟吲哚的有效策略，即N-杂环卡宾（NHC）催化二醇的去对称化反应。该过程基于使用易得的醛作为酰化剂对伯醇进行催化不对称转移酰化反应。该反应能够以优异的对映选择性轻松获得多种功能化的C3-季碳羟吲哚。通过制备（-）-依色麦角林和（-）-毒扁豆碱的关键中间体，进一步证明了该过程的合成潜力。
