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A detailed investigation of the aza-Prins reaction

A detailed investigation of the aza-Prins reaction

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Dobbs, Adrian P., 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:10.1039/B915797B)

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Abstract

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 / Department / Research Group: Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 17 Oct 2016 09:12
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/9982

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