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A detailed investigation of the aza-Prins reaction

A detailed investigation of the aza-Prins reaction

Dobbs, Adrian P. ORCID: 0000-0002-7241-7118, Guesné, Sebastien J.J., Parker, Robert J., Skidmore, John, Stephenson, Richard A. and Hursthouse, Mike B. (2010) A detailed investigation of the aza-Prins reaction. Organic & Biomolecular Chemistry, 8 (5). pp. 1064-1080. ISSN 1477-0520 (Print), 1477-0539 (Online) (doi:

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The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s).

Item Type: Article
Additional Information: [1] First published online 05 Jan 2010. [2] Electronic supplementary information (ESI) available: The preparation of, and characterisation data for, the precursor alcohols, their tosyl derivatives, and for the N-tosyl amines, and full details concerning the unsuccessful Lewis acid screening conditions. CCDC reference numbers 748949–748951. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/b915797b.
Uncontrolled Keywords: Lewis acid, aza-Prins reaction, piperidines, pyrrolidines
Subjects: Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science > School of Science (SCI)
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Last Modified: 21 Oct 2020 22:31

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