Craig Ryan, Sorrentino Emiliano, Connon Stephen J
Synthesis and Solid State Pharmaceutical Centre, Trinity Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin, 2, Ireland.
Chemistry. 2018 Mar 26;24(18):4528-4531. doi: 10.1002/chem.201800313. Epub 2018 Mar 7.
A new bifunctional phase-transfer catalyst that employs hydrogen bonding as a control element was developed to promote efficient enantioselective S 2 reactions for the construction all-carbon quaternary stereocenters in high yield and excellent enantioselectivity (up to 97 % ee) utilizing the alkylation of a malleable oxindole substrate. The utility of the methodology was demonstrated through a concise and highly enantioselective synthesis of (-)-debromoflustramine B.
开发了一种新型双功能相转移催化剂，该催化剂利用氢键作为控制元素，以促进高效对映选择性S2反应，通过可塑的氧化吲哚底物的烷基化反应，高收率、高对映选择性（高达97%ee）地构建全碳季立体中心。通过简洁且高度对映选择性的合成（-）-去溴弗拉斯特拉明B证明了该方法的实用性。
