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Investigation of the Corey Bromolactamization withN-Functionalized Allylamines
- Source :
- Journal of Heterocyclic Chemistry. 53:1827-1837
- Publication Year :
- 2015
- Publisher :
- Wiley, 2015.
-
Abstract
- N-Allylamines were employed for the diastereoselective synthesis of 8-bromo-substituted, cis-configured perhydroquinoxalines and β-bromoalcohols. The yield and constitution of the products depend considerably on the functionalization of the allylic N-atom. Herein the reaction of glycine-derived cyclohex-2-enamines under bromolactamization conditions (LiOtBu, NBS) is reported. Methyl carbamate led diastereoselectively to the cis-configured perhydroquinoxaline , whereas the amides and provided cis,trans-configured -bromoalcohols and . Based on high level theoretical calculations (DFT) factors controlling the cyclization of lithiated intermediates and the relative energies of possible products are discussed.
Details
- ISSN :
- 0022152X
- Volume :
- 53
- Database :
- OpenAIRE
- Journal :
- Journal of Heterocyclic Chemistry
- Accession number :
- edsair.doi...........9429e19029652477ea088befd737884a