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Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde

Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde
Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde
The proline-catalyzed aldol reaction of racemic 2-(2?-pyrimidyl)ferrocenecarbaldehyde with acetone in DMSO at room temperature constitutes as the first example of an organocatalytic kinetic resolution of a planar-chiral compound. The selectivity factor of the kinetic resolution is 9.2, and the stereochemical outcome of the process can be easily rationalized by the standard mechanistic model of the proline-catalyzed aldol reaction.
0957-4166
1314-1318
Alba, Andrea-Nekane
e96df5c1-b984-45c5-9620-1d7f0cec8faf
Gómez-Sal, Pilar
36b7e4ab-65a5-4a59-bf84-23e1dc21c1eb
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Alba, Andrea-Nekane
e96df5c1-b984-45c5-9620-1d7f0cec8faf
Gómez-Sal, Pilar
36b7e4ab-65a5-4a59-bf84-23e1dc21c1eb
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa

Alba, Andrea-Nekane, Gómez-Sal, Pilar, Rios, Ramon and Moyano, Albert (2009) Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde. Tetrahedron: Asymmetry, 20 (11), 1314-1318. (doi:10.1016/j.tetasy.2009.05.011).

Record type: Article

Abstract

The proline-catalyzed aldol reaction of racemic 2-(2?-pyrimidyl)ferrocenecarbaldehyde with acetone in DMSO at room temperature constitutes as the first example of an organocatalytic kinetic resolution of a planar-chiral compound. The selectivity factor of the kinetic resolution is 9.2, and the stereochemical outcome of the process can be easily rationalized by the standard mechanistic model of the proline-catalyzed aldol reaction.

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Published date: 19 June 2009
Organisations: Chemistry
Learn more about Chemistry research

Identifiers

Local EPrints ID: 347727
URI: http://eprints.soton.ac.uk/id/eprint/347727
DOI: doi:10.1016/j.tetasy.2009.05.011
ISSN: 0957-4166
PURE UUID: e20d415e-7809-42a1-acaa-b07b3c8471b3
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 29 Jan 2013 13:13
Last modified: 14 Mar 2024 12:51

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Contributors

Author: Andrea-Nekane Alba
Author: Pilar Gómez-Sal
Author: Ramon Rios ORCID iD
Author: Albert Moyano

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