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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.

Original publication

DOI

10.1016/S0040-4039(99)00391-3

Type

Journal article

Journal

Tetrahedron Letters

Publication Date

09/04/1999

Volume

40

Pages

2907 - 2908