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

Hung-Yang Chen; Laxmikant N. Patkar; Shau-Hua Ueng; Chun-Cheng Lin; Adam Shih-Yuan Lee

doi:10.1055/s-2005-871934

LETTER

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

Hung-Yang Chen^a, Laxmikant N. Patkar^b, Shau-Hua Ueng^b, Chun-Cheng Lin*^b,c, Adam Shih-Yuan Lee*^a
^a Department of Chemistry, Tamkang University, Tamsui, Taiwan
^b Institute of Chemistry and Genomic Research Center, Academia Sinica, Taipei, Taiwan
^c Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan
Fax: +88(62)26223830; e-Mail: adamlee@mail.tku.edu.tw;

Abstract

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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_N2′ product 7 was produced using dichloromethane as a solvent and triethylamine (7 equiv) as base; S_N2 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 α-methylene β-lactam 8 using Sn[N(TMS)₂]₂ as a reagent, is disclosed.

Key words

β-amino ester - amination - regioselectivity - α-methylene β-lactam - allyl bromide

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References

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