33447-72-2Relevant articles and documents
An Asymmetric Transformation of Symmetrical Epoxides to Both Enantimers of Allylic Alcohols by Chiral Lithium Amides
Asami, Masatoshi,Kirihara, Hiroto
, p. 389 - 392 (1987)
Both enantiomers of several optically active allylic alcohols are obtained from cyclic and acyclic symmetrical epoxides by using chiral lithium amides, i.e., lithium cyclohexylmethylamide or lithium (S)-2-pyrrolidide, as bases.
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.
METHOD FOR PRODUCING 3-BUTENE-2-OL
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Paragraph 0073; 0074, (2016/11/07)
PROBLEM TO BE SOLVED: To provide a method for efficiently producing racemic 3-butene-2-ol having an (S)- or (R)-configuration. SOLUTION: There is provided a method for producing racemic 3-butene-2-ol, wherein an ammonium salt compound represented by the following general formula (1) (wherein, R1, R2 or R3 represents an alkyl group, an aryl group or an aralkyl group; X- represents OH-, HCO3-, CO32-, R4O-, R5CO2-, R6SO3- (R4, R5 or R6 represents an alkyl group, an aryl group or an aralkyl group) and a halide ion; n represents 0.5 when X- is CO32- and n represents 1 when X- is other than CO32-; the carbon atom marked with * is an asymmetric carbon atom) is subjected to Hofmann elimination. COPYRIGHT: (C)2016,JPOandINPIT
Inclusion of aliphatic alcohols in pockets of (S)-threonyl-(S)- phenylglycine using grinding method
Akazome, Motohiro,Toma, Shusaku,Horiguchi, Tatsunori,Megumi, Ken,Matsumoto, Shoji
experimental part, p. 2844 - 2848 (2011/05/06)
Inclusion compounds of a dipeptide, (S)-threonyl-(S)-phenylglycine (Thr-Phg), with several aliphatic alcohols were easily prepared by grinding them in a mortar. Thr-Phg molecules arranged in antiparallel to construct a sheet, and guest alcohols were accommodated in a chiral pocket between the sheets. 3-Butyn-2-ol and 2-butanol were included with moderate enantioselectivity, 57% ee (R) and 49% ee (R), respectively. The role of the hydroxy group of Thr-Phg is not only to construct the unique pocket but also to capture guest alcohols by hydrogen bonding.