Asymmetric ‘Clip-Cycle’ synthesis of 3-spiropiperidines
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 <i>E</i>-selective cross metathesis of <i>N</i>-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.
Authors
- William P. Unsworth (ORCID: https://orcid.org/0000-0002-9169-5156)
- Paul A. Clarke (ORCID: https://orcid.org/0000-0003-3952-359X)
- Ian J. S. Fairlamb (ORCID: https://orcid.org/0000-0002-7555-2761)
- Christopher J. Maddocks (ORCID: https://orcid.org/0000-0003-0851-0569)
- Saikiran Ravi
Institutions
- University of York (GB)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2024-11-20
- DOI
- https://doi.org/10.1039/d4ob01608d
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- University of York
- Royal Society