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A detailed investigation of the aza-Prins reaction

A detailed investigation of the aza-Prins reaction
A detailed investigation of the aza-Prins reaction
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).
1477-0520
1064-1080
Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54
Guesné, Sebastien J.J.
5c746d98-0c89-499d-927f-014e8af83b28
Parker, Robert J.
a3a6bf55-8309-426f-8621-a28599edb476
Skidmore, John
53f63731-e26e-484e-a901-701415aa5066
Stephenson, Richard A.
f92145c3-799d-4f3b-afe7-4d3fc7da8b30
Hursthouse, Mike B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54
Guesné, Sebastien J.J.
5c746d98-0c89-499d-927f-014e8af83b28
Parker, Robert J.
a3a6bf55-8309-426f-8621-a28599edb476
Skidmore, John
53f63731-e26e-484e-a901-701415aa5066
Stephenson, Richard A.
f92145c3-799d-4f3b-afe7-4d3fc7da8b30
Hursthouse, Mike B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

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), 1064-1080. (doi:10.1039/b915797b). (PMID:20165797)

Record type: Article

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).

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More information

e-pub ahead of print date: 5 January 2009
Published date: March 2010
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 347446
URI: http://eprints.soton.ac.uk/id/eprint/347446
ISSN: 1477-0520
PURE UUID: 36b61f56-39a4-43da-ae15-b94b72249868

Catalogue record

Date deposited: 24 Jan 2013 14:40
Last modified: 16 Jul 2019 21:45

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