6118-13-4Relevant articles and documents
Are Highly Stable Covalent Organic Frameworks the Key to Universal Chiral Stationary Phases for Liquid and Gas Chromatographic Separations?
Cui, Yong,Jia, Wenyan,Li, Yanan,Yu, Ziyun,Yuan, Chen,Yuan, Li-Ming,Zi, Min
, p. 891 - 900 (2022/02/03)
High-performance liquid chromatography (HPLC) and gas chromatography (GC) over chiral stationary phases (CSPs) represent the most popular and highly applicable technology in the field of chiral separation, but there are currently no CSPs that can be used for both liquid and gas chromatography simultaneously. We demonstrate here that two olefin-linked covalent organic frameworks (COFs) featuring chiral crown ether groups can be general CSPs for extensive separation not only in GC but also in normal-phase and reversed-phase HPLC. Both COFs have the same 2D layered porous structure but channels of different sizes and display high stability under different chemical environments including water, organic solvents, acids, and bases. Chiral crown ethers are periodically aligned within the COF channels, allowing for enantioselective recognition of guest molecules through intermolecular interactions. The COF-packed HPLC and GC columns show excellent complementarity and each affords high resolution, selectivity, and durability for the separation of a wide range of racemic compounds, including amino acids, esters, lactones, amides, alcohols, aldehydes, ketones, and drugs. The resolution performances are comparable to and the versatility is superior to those of the most widely used commercial chiral columns, showing promises for practical applications. This work thus advances COFs with high stability as potential universal CSPs for chromatography that are otherwise hard or impossible to produce.
H-bonding as a control element in stereoselective Ru-catalyzed olefin metathesis
Hoveyda, Amir H.,Lombardi, Pamela J.,O'Brien, Robert V.,Zhugralin, Adil R.
supporting information; experimental part, p. 8378 - 8379 (2009/10/23)
(Chemical Equation Presented) H-bonding interactions have been exploitedextensively in the design of catalysts for stereoselective synthesis bu t have rarely been utilized in the development of metal-catalyzed processes. Studies described herein demonstrate that intramolecular H-bonding interactions can significantly increase the rate and levels of stereochemical control in Ru-catalyzed olefin metathesis reactions. The utility of H-bonding in catalytic olefin metathesis is elucidated through development of exceptionally facile and highly diastereoselective ring-opening/cross-metathesis (DROCM) reactions, involving achiral Ru catalysts and enantiomerically enriched allylic alcohols. Transformations proceed to completion readily (>98percent conversion, up to 87percent yield), often within minutes, in the presence of ≤2 mol percent of an achiral catalyst to afford synthetically versatile products of high stereochemical purity (up to >98:2 dr and 11:1 E:Z).
Asymmetric trasformation of symmetrical epoxides to allylic alcohols by lithium (S)-2-(N,N-disubstituted aminomethyl)pyrrolidide
Asami
, p. 721 - 727 (2007/10/02)
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