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Organocatalytic cyclopropanation of (E)-Dec-2-enal: Synthesis, spectral analysis and mechanistic understanding

Organocatalytic cyclopropanation of (E)-Dec-2-enal: Synthesis, spectral analysis and mechanistic understanding
Organocatalytic cyclopropanation of (E)-Dec-2-enal: Synthesis, spectral analysis and mechanistic understanding
An undergraduate experiment combining synthesis, NMR analysis and mechanistic understanding is reported. The students perform an organocatalyzed cyclopropanation reaction of (E)-dec-2-enal and are then required to determine the diastereoselectivity and assign the relative configuration of each product using NMR spectroscopy.
Upper Division Undergraduates, Organic Chemistry, HAnd-On Learning/Manipulatives, Inquiry-based/Discovery Learning, Asymmetric Synthesis, NMR Spectroscopy, Diastereomers
0021-9584
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Kowalczuk, Agnieszka
5acf6d9e-655e-4cd8-897f-f5e20f75a1d1
Watkins, Sarah
75208c93-c0cd-4c35-ad07-cea91597501b
Holland, Simon
e0afa720-08a1-4519-85d6-d508a96e29df
Logothetis, Thomas
9f42a28f-0c36-4d47-a137-7a317acb0237
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Kowalczuk, Agnieszka
5acf6d9e-655e-4cd8-897f-f5e20f75a1d1
Watkins, Sarah
75208c93-c0cd-4c35-ad07-cea91597501b
Holland, Simon
e0afa720-08a1-4519-85d6-d508a96e29df
Logothetis, Thomas
9f42a28f-0c36-4d47-a137-7a317acb0237
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Meazza, Marta, Kowalczuk, Agnieszka, Watkins, Sarah, Holland, Simon, Logothetis, Thomas and Rios, Ramon (2018) Organocatalytic cyclopropanation of (E)-Dec-2-enal: Synthesis, spectral analysis and mechanistic understanding. Journal of Chemical Education. (doi:10.1021/acs.jchemed.7b00566).

Record type: Article

Abstract

An undergraduate experiment combining synthesis, NMR analysis and mechanistic understanding is reported. The students perform an organocatalyzed cyclopropanation reaction of (E)-dec-2-enal and are then required to determine the diastereoselectivity and assign the relative configuration of each product using NMR spectroscopy.

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Manuscript JCE July 2018 - Accepted Manuscript
Available under License University of Southampton Accepted Manuscript Licence.
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Accepted/In Press date: 9 August 2018
e-pub ahead of print date: 9 August 2018
Keywords: Upper Division Undergraduates, Organic Chemistry, HAnd-On Learning/Manipulatives, Inquiry-based/Discovery Learning, Asymmetric Synthesis, NMR Spectroscopy, Diastereomers
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Identifiers

Local EPrints ID: 424787
URI: http://eprints.soton.ac.uk/id/eprint/424787
DOI: doi:10.1021/acs.jchemed.7b00566
ISSN: 0021-9584
PURE UUID: c2e9815c-7004-4f3d-bd5d-40eb957e714b
ORCID for Marta Meazza: ORCID iD orcid.org/0000-0003-4382-0626
ORCID for Thomas Logothetis: ORCID iD orcid.org/0000-0002-3437-5287
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 05 Oct 2018 11:45
Last modified: 16 Mar 2024 06:59

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Contributors

Author: Marta Meazza ORCID iD
Author: Agnieszka Kowalczuk
Author: Sarah Watkins
Author: Simon Holland
Author: Thomas Logothetis ORCID iD
Author: Ramon Rios ORCID iD

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