Stereocontrolled synthesis and alkylation of cyclic beta-amino esters: asymmetric synthesis of a (-)-sparteine surrogate.
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.
Hermet
Jean-Paul R
JP
Department of Chemistry, University of York, Heslington, York, UK.
Viterisi
Aurélien
A
Wright
Jonathan M
JM
McGrath
Matthew J
MJ
O'Brien
Peter
P
Whitwood
Adrian C
AC
Gilday
John
J
D000478:Alkylation; D018360:Crystallography, X-Ray; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D013034:Sparteine / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D013034:Sparteine