1312366-20-3Relevant academic research and scientific papers
Method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by one-pot method
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Paragraph 0047-0050; 0055; 0270-0281, (2020/12/15)
The invention relates to a method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by a one-pot method. The method comprises the following steps: making a racemic alpha-allyl alcohol compound, an amine compound, a chiral ruthenium complex and an alkaline reagent react in an organic solvent, and carrying out separation and purification after completion of the reaction, so that chiral gamma-aminoalcohols and chiral alpha-allylalcohol are prepared, wherein a chiral ruthenium complex is selected from one of them. According to the preparation method of the chiral compound, two chiral compounds with wide purposes, namely the chiral gamma-amino alcohol and the chiral alpha-allyl alcohol, are obtained at the same time through a one-pot reaction, the reaction is simple, the atom economy is high, few by-products are produced, and the requirements of green chemistry are met.
Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs
Wang, Pei,Ma, Guo-Rong,Yu, Sheng-Li,Da, Chao-Shan
supporting information, p. 79 - 86 (2018/12/13)
Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.
Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols
Musolino, Stefania F.,Ojo, O. Stephen,Westwood, Nicholas J.,Taylor, James E.,Smith, Andrew D.
supporting information, p. 18916 - 18922 (2016/12/26)
The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.
Ruthenium-catalyzed regio- and enantioselective allylic substitution with water: Direct synthesis of chiral allylic alcohols
Kanbayashi, Naoya,Onitsuka, Kiyotaka
supporting information; experimental part, p. 5197 - 5199 (2011/06/26)
Less is more: A new route to access chiral allylic alcohols through the regio- and enantioselective substitution of monosubstituted allylic chlorides with water has been developed. The reaction is catalyzed effectively by planar-chiral cyclopentadienyl ruthenium complexes (see scheme). Copyright
