Title: Synthesis of beta-amino esters by regioselective amination of allyl bromides with aryl and alkyl amines
Authors: Chen, HY
Patkar, LN
Ueng, SH
Lin, CC
Lee, ASY
Department of Applied Chemistry
Keywords: beta-amino ester;amination;regioselectivity;alpha-methylene beta-lactam;allyl bromide
Issue Date: 19-Aug-2005
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.
URI: http://dx.doi.org/10.1055/s-2005-871934
ISSN: 0936-5214
DOI: 10.1055/s-2005-871934
Journal: SYNLETT
Issue: 13
Begin Page: 2035
End Page: 2038
Appears in Collections:Articles

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