Direct Organocatalytic Enantioselective Functionalization of SiO x Surfaces
Direct Organocatalytic Enantioselective Functionalization of SiO x Surfaces
复制标题
SiO x 表面的直接有机催化对映选择性功能化
DOI：
10.1002/ange.201804814
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发表时间：
2018
影响因子：
--
通讯作者：
Parkin J
中科院分区：
文献类型：
--
作者：
Parkin J
制备手性表面的传统方法包括将手性分子吸附到非手性表面上，或吸附形成手性模板的物质，从而产生具有长范围有序的晶格。迄今为止，只研究了有限的制备手性表面的替代策略。在这篇论文中，开发了一种“自下而上”的方法，允许在功能化氧化硅支持的自组装单层（SAM）上通过直接对映选择性有机催化反应制备手性表面。利用市售的均相异硫脲催化剂，在氧化硅负载的具有活性三氟酮官能团的SAM上促进对映选择性Michael -内酯化过程，实现了对映体富集有机表面的高效催化生成。手性原子力显微镜（χ - AFM）通过测量由d - l -半胱氨酸修饰的AFM尖端与有机膜相互作用产生的力分布来探测有机膜的对映体富集。
Traditional methods to prepare chiral surfaces involve either the adsorption of a chiral molecule onto an achiral surface, or adsorption of a species that forms a chiral template creating lattices with long range order. To date only limited alternative strategies to prepare chiral surfaces have been studied. In this manuscript a “bottom‐up” approach is developed that allows the preparation of chiral surfaces by direct enantioselective organocatalytic reactions on a functionalized silicon oxide supported self‐assembled monolayer (SAM). The efficient catalytic generation of enantiomerically enriched organic surfaces is achieved using a commercially available homogeneous isothiourea catalyst that promotes an enantioselective Michael‐lactonization process upon a silicon‐oxide supported SAM functionalized with a reactive trifluoroenone group. Chiral atomic force microscopy (χ‐AFM) is used to probe the enantiomeric enrichment of the organic films by measurement of the force distributions arising from interaction ofd‐ orl‐cysteine‐modified AFM tips and the organic films.