Organocatalytic Cyclopropanation of (E)-Dec-2-enal: Synthesis, Spectral Analysis and Mechanistic Understanding

Marta Meazza; Agnieszka Kowalczuk; Sarah Watkins; Simon Holland; Thomas A. Logothetis; Ramon Rios

doi:10.1021/acs.jchemed.7b00566

Organocatalytic Cyclopropanation of (E)-Dec-2-enal: Synthesis, Spectral Analysis and Mechanistic Understanding

Marta Meazza
, Agnieszka Kowalczuk
, Sarah Watkins
, Simon Holland
, Thomas A. Logothetis
, Ramon Rios

Chemistry

University of Southampton

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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.

Original language	British English
Pages (from-to)	1832-1839
Number of pages	8
Journal	Journal of Chemical Education
Volume	95
Issue number	10
DOIs	https://doi.org/10.1021/acs.jchemed.7b00566
State	Published - 9 Oct 2018

Keywords

Asymmetric Synthesis
Diastereomers
Hands-On Learning/Manipulatives
Inquiry-Based/Discovery Learning
NMR Spectroscopy
Organic Chemistry
Upper Division Undergraduate

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title = "Organocatalytic Cyclopropanation of (E)-Dec-2-enal: Synthesis, Spectral Analysis and Mechanistic Understanding",

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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AU - Watkins, Sarah

AU - Holland, Simon

AU - Logothetis, Thomas A.

AU - Rios, Ramon

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AB - 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.

KW - Asymmetric Synthesis

KW - Diastereomers

KW - Hands-On Learning/Manipulatives

KW - Inquiry-Based/Discovery Learning

KW - NMR Spectroscopy

KW - Organic Chemistry

KW - Upper Division Undergraduate

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Organocatalytic Cyclopropanation of (E)-Dec-2-enal: Synthesis, Spectral Analysis and Mechanistic Understanding

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Keywords

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