Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of β,γ-Unsaturated Ketones

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Title:	Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of β,γ-Unsaturated Ketones
Authors:	Lee, Adam Shih-yuan;Wang, Shu-huei;Chang, Yu-ting;Chu, Shu-fang
Contributors:	淡江大學化學學系
Keywords:	β,γ-unsaturated ketone;β-amino ketone;β-methoxy ketone;α,β-unsaturated ketone;1,4-addition reaction
Date:	2003-12
Issue Date:	2009-12-01
Publisher:	Stuttgart: Georg Thieme Verlag
Abstract:	A reaction mixture of β,γ-unsaturated ketone and BF3·OEt2 in CH3OH was stirred at room temperature and β-methoxy ketone was produced in high yield. The β-amino ketone was obtained as the major product from a reaction mixture of β,γ-unsaturated ketone, AlCl3 and Ts-NH2 in CH2Cl2 at room temperature. This Lewis acid promoted β-substitution reaction mechanism was proposed as that the process occurred via in situ isomerization of β,γ-unsaturated ketone to α,β-unsaturated ketone followed by the 1,4-addition reaction.
Relation:	Synlett 2003(15), pp.2359-2363
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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