439828-63-4Relevant academic research and scientific papers
Synthesis method of fructose-derived chiral ketone catalyst
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Paragraph 0018; 0019; 0020; 0037; 0038; 0039, (2016/10/10)
The invention provides a synthesis method of a fructose-derived chiral ketone catalyst. The method comprises the following steps: (1) by using D-fructose and acetone as a raw material, carrying out ketonization reaction at 10-45 DEG C by using concentrated sulfuric acid as a catalyst to obtain a first intermediate; (2) dissolving the first intermediate in an organic solvent, adding molecular sieve powder, and carrying out oxidation at 50-80 DEG C by using PCC as an oxidant, thereby obtaining a second intermediate; (3) carrying out hydrolysis on the second intermediate at 10-45 DEG C under the actions of acetic acid, water and zinc chloride, thereby obtaining a third intermediate; after the hydrolysis finishes, adding acetic anhydride, and carrying out esterification reaction to obtain a fructose-derived chiral ketone hydrate; and (4) eliminating water molecules in the fructose-derived chiral ketone hydrate by using a polar organic solvent, thereby obtaining the fructose-derived chiral ketone. The method has the advantages of simple technique, low raw material cost and mild reaction conditions, is convenient for separation and purification, can be used for quickly and efficiently synthesizing the fructose-derived chiral ketone catalyst, and is more suitable for industrial production.
Efficient magnetic and recyclable SBILC (supported basic ionic liquid catalyst)-based heterogeneous organocatalysts for the asymmetric epoxidation of trans-methylcinnamate
Candu,Rizescu,Podolean,Tudorache,Parvulescu,Coman
, p. 729 - 737 (2015/02/19)
A green alternative, based on the use of an efficient and recyclable chiral ketone@SBILC@MWCNT@Fe3O4 catalytic system (Y = 35%, S = 100% and ee = 100%), was developed for the asymmetric epoxidation of trans-methylcinnamate to (2R,3S)
Unprecedented 8,9′-neolignans: Enantioselective synthesis of possible stereoisomers for structural determination
Takahashi, Masato,Suzuki, Noriyuki,Ishikawa, Tsutomu,Huang, Hung-Yi,Chang, Hsun-Shuo,Chen, Ih-Sheng
, p. 2585 - 2589 (2015/02/05)
(+)-Wutaienin (3) and its C-7 methyl ether (4), isolated from Zanthoxylum wutaiense, were found to be unprecedented 8,9′-neolignans containing an (S)-2-(1,1-dimethyl-1-hydroxymethyl)-7-methoxydihydrobenzofuran skeleton. Wutaienin (3) was present in the pl
A diacetate ketone-catalyzed asymmetric epoxidation of olefins
Wang, Bin,Wu, Xin-Yan,Wong, O. Andrea,Nettles, Brian,Zhao, Mei-Xin,Chen, Dajun,Shi, Yian
experimental part, p. 3986 - 3989 (2009/09/30)
(Chemical Equation Presented) A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient α,β-unsaturated esters as well as certain cis olefins.
Practical synthesis of Shi's diester fructose derivative for catalytic asymmetric epoxidation of alkenes
Nieto,Molas,Benet-Buchholz,Vidal-Ferran
, p. 10143 - 10146 (2007/10/03)
A practical synthesis of Shi's diester 3 for catalytic asymmetric epoxidations has been developed. The catalyst has been prepared in multigram quantities from D-fructose in four steps with a 66% overall yield. Efficiency, cost, and selectivity aspects of the reagents involved for its preparation have been taken care of during its preparation. The workup procedures have been simplified to the bare minimum, rendering a very practical preparation method. The well-known high efficiency of this catalyst 3 in the epoxidation of α,α-unsaturated carbonyl compounds has also proved to be high in unfunctionalized alkenes.
Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane
Wu, Xin-Yan,She, Xuegong,Shi, Yian
, p. 8792 - 8793 (2007/10/03)
This paper describes a highly enantioselective epoxidation of α,β-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82-98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's. Copyright
