Synthesis of β-Amino Esters by Regioselective Amination of Allyl Bromides with Aryl and Alkyl Amines

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Title:	Synthesis of β-Amino Esters by Regioselective Amination of Allyl Bromides with Aryl and Alkyl Amines
Authors:	Lee, Adam Shih-yuan;Chen, Hung-Yang;Patkar, Laxmikant N.;Ueng, Shau-hua;Lin, Chun-cheng
Contributors:	淡江大學化學學系
Keywords:	β-amino ester;amination;regioselectivity;α-methylene β-lactam;allyl bromide
Date:	2005-08
Issue Date:	2009-12-01
Publisher:	Stuttgart: Georg Thieme Verlag
Abstract:	One of the two possible regioisomers can be exclusively formed by combining a suitable solvent and a specific amount of triethylamine as a base during the amination of allyl bromide 5. The S(N)2' product 7 was produced using dichloromethane as a solvent and triethylamine (7 equiv) as base; S(N)2 product 6 was predominantly generated in hexane with 0.5 equivalents of triethylamine. Furthermore, a new reaction condition for the efficient cyclization of 7 to yield alpha-methylene beta-lactam 8 using Sn[N(TMS)(2)](2) as a reagent, is disclosed.
Relation:	Synlett 2005(13), pp.2035-2038
DOI:	10.1055/s-2005-871934
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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