3-Spiropiperidines can be synthesized in up to 87% yield and 96 : 4 er using a two step ‘Clip-Cycle’ approach. The ‘Clip’ stage of this method is based on efficient and highly E-selective cross metathesis of N-Cbz-protected 1-amino-hex-5-enes with a thioacrylate. This is followed by the ‘Cycle’ step, in which an intramolecular asymmetric aza-Michael cyclization is promoted by a chiral phosphoric acid catalyst.
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S. Ravi, C. J. Maddocks, I. J. S. Fairlamb, W. P. Unsworth and P. A. Clarke, Org. Biomol. Chem., 2025, 23, 649 DOI: 10.1039/D4OB01608D
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