Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation
Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation
复制标题
DOI：
10.1039/c4sc01440e
复制
发表时间：
2014-01-01
期刊：
影响因子：
8.4
通讯作者：
Miller, Scott J.
中科院分区：
文献类型：
--
作者：
Abascal, Nadia C.;Lichtor, Phillip A.;Miller, Scott J.
我们详细研究了一种肽基催化剂（6），该催化剂对法尼醇的位点-（>100：1：1）和对映选择性环氧化（86%ee）有效。研究了催化剂的底物范围，沿着探索了最佳反应条件。机制的研究报告，包括催化剂和丙酸的相对速率测定，历史的观点，截断的研究，并使用NMR数据建模。我们汇编的数据推进了我们对通过组合方法确定的催化剂内部工作原理的理解。
We detail an investigation of a peptide-based catalyst (6) that is effective for the site- (>100 : 1 : 1) and enantioselective epoxidation (86% ee) of farnesol. Studies of the substrate scope exhibited by the catalyst are included, along with an exploration of optimized reaction conditions. Mechanistic studies are reported, including relative rate determinations for the catalyst and propionic acid, a historical perspective, truncation studies, and modeling using NMR data. Our compiled data advances our understanding of the inner workings of a catalyst that was identified through combinatorial means.