Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold. Dolle, R., E., Barden, M., C., Brennan, P., E., Ahmed, G., Tran, V., & Ho, D., M. Tetrahedron Letters, 40(15):2907-2908, Elsevier Science Ltd., 1999.
Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold [pdf]Paper  Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold [link]Website  doi  abstract   bibtex   1 download  
Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecular azomethine imine cyctoaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.

Downloads: 1