AI Article Synopsis
- A method for making cyclic beta-amino esters has been developed using iodo alphabeta-unsaturated esters and alpha-methylbenzylamine, ensuring stereoselectivity.
- Subsequent steps involve generating enolates and alkylating them effectively, taking advantage of the interactions between two stereogenic centers.
- This approach has been successfully applied to synthesize a functionalized piperidine, which is useful for creating alkaloid natural products, including a (-)-sparteine surrogate.
Article Abstract
A convenient method for the stereoselective synthesis of cyclic beta-amino esters from an iodo alphabeta-unsaturated ester and alpha-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (-)-sparteine surrogate.
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| http://dx.doi.org/10.1039/b712503h | DOI Listing |
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