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Synthesis of β-amino esters by regioselective amination of allyl bromides with aryl and alkyl amines
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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 LinAdam Shih-Yuan Lee
Synlett, (13), 頁碼.2035-2038
08/2005

摘要

α-methylene β-lactam β-amino ester Allyl bromide Amination Regioselectivity Organic Chemistry
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 α-methylene β-lactam 8 using Sn[N(TMS) 2 ] 2 as a reagent, is disclosed. © Georg Thieme Verlag Stuttgart.

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