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Asymmetric Synthesis of α-fluoromethylated α-propargylamines Induced by (S)-tert-butanesulfinamide

Author: ChenHui
Tutor: HuangYanGen
School: Donghua University
Course: Organic Chemistry
Keywords: Asymmetric Synthesis 1,2 - addition (S) - tert - propanesulfinamide α- difluoromethyl -α- propargylamine α - monofluoromethyl -α- propargylamine
CLC: O621.34
Type: Master's thesis
Year: 2012
Downloads: 15
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Abstract


In recent years , in the asymmetric synthesis of a fluorine - containing amine compound , a chiral auxiliary group tert propanesulfinamide attracted the concern of many chemists . Aldehyde ketone tert propanesulfinamide with fluorine generated imine and 1,2 - addition reaction occurs , and then with an organometallic reagent , and may be asymmetric to achieve selectively the synthesis of fluorine - containing amine compound . First part: first to (SS) - tert - butylimino sulfonamide as raw materials , in the presence of a Lewis acid difluoromethyl ketone produced in the dehydration condensation of Ti (OEt ) 4 catalyzed difluoromethyl substituted chiral substituted tert-butoxy alkylsulfinyl ketimine , and then 1,2 - nucleophilic addition reaction with lithium alkynyl depth study, a good yield ( 51-93 %) and excellent diastereoselective ( 85:15-93:7 ) Synthesis of a series of chiral α-difluoro methyl α- propargyl sulfenamide derivatives , and finally take off in the HCl / 1,4-dioxane system tert-butyl sulfonyl group, a high yield (90-95%) to give the corresponding optically pure α- difluoro- methyl α- propargylamine 5 . Plays a key role in the Lewis acid is Ti (OiPr) 4 on the production rate of increase in this addition reaction , Moreover, with respect to non-fluorinated substrates , difluoromethyl methyl groups enhance the reactivity of the imine and improve diastereoselective reaction . Part II: The method of the previous chapter established system for the synthesis of α - monofluoro methyl α- propargylamine attempt, using direct fluorination reagent the Selectfluor with an aryl group (hydrocarbyl ) ethanone under microwave conditions for direct fluorination reaction monofluoro substituted aryl (hydrocarbyl) -ethanone, then the the feedstock with tert - propanesulfinamide reaction monofluoromethyl methyl substituted ketimines, due to the lower stability of imine hydrolysis , after purification directly to the next step with the addition reaction of lithium alkynyl . Try a different solvent and Lewis acid ( Ti (OEt ) system 4/THF , BF3 Et2O/THF and the Ti ( OEt ) 4/n-Hexane ) , but in the end did not target product α - monofluoromethyl α derivatives of - propargylamine .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Synthetic organic chemistry > Asymmetric Organic Synthesis
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