Choi, A., Castle, J., Saruengkhanphasit, R. et al. (1 more author) (2020) Synthesis of spirocyclic amines by 1,3-dipolar cycloaddition of azomethine ylides and azomethine imines. Synthesis, 52 (08). pp. 1273-1278. ISSN 0039-7881
Abstract
Simple ketone starting materials with a halide leaving group and an alkene were prepared in one step and heated with glycine or glycine esters to promote a tandem imine formation, cyclization, and dipolar cycloaddition cascade. The chemistry was also feasible with acetylhydrazide. In each case a single stereoisomer of the tricyclic amine or pyrazolidine product was formed and the stereochemistry was verified by single crystal X-ray diffraction. When the reaction with glycine, which occurs with loss of CO2, was unsuccessful, the cascade process could be promoted by cross metathesis to give the vinyl sulfone starting material that provides a more reactive dipolarophile. Reductive cleavage of the pyrazolidine gave a spirocyclic diamine product.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2020 Thieme. This is an author-produced version of a paper subsequently published in Synthesis. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | amines; cyclization; cycloaddition; diastereoselectivity; spiro compounds |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 12 Feb 2020 12:23 |
Last Modified: | 09 Dec 2021 13:30 |
Status: | Published |
Publisher: | Thieme |
Refereed: | Yes |
Identification Number: | 10.1055/s-0039-1691588 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:156821 |