Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde

Andrea Nekane Alba; Pilar Gómez-Sal; Ramon Rios; Albert Moyano

doi:10.1016/j.tetasy.2009.05.011

Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde

Andrea Nekane Alba
, Pilar Gómez-Sal
, Ramon Rios
, Albert Moyano

Chemistry

Universitat de Barcelona
Universidad de Alcalá

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

36 Scopus citations

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.

Original language	British English
Pages (from-to)	1314-1318
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	20
Issue number	11
DOIs	https://doi.org/10.1016/j.tetasy.2009.05.011
State	Published - 19 Jun 2009

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title = "Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde",

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.",

author = "Alba, \{Andrea Nekane\} and Pilar G{\'o}mez-Sal and Ramon Rios and Albert Moyano",

note = "Funding Information: We thank the Spanish Ministry of Science and Education for financial support (Project AYA2006-15648-C02-01). P.G.-S. is also indebted to {\textquoteleft}Factor{\'i}a de Cristalizaci{\'o}n{\textquoteright} (Consolider-Ingenio 2010). A.-N.A. is grateful to the University of Barcelona for an APIF pre-doctoral fellowship.",

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doi = "10.1016/j.tetasy.2009.05.011",

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AU - Alba, Andrea Nekane

AU - Gómez-Sal, Pilar

AU - Rios, Ramon

AU - Moyano, Albert

N1 - Funding Information: We thank the Spanish Ministry of Science and Education for financial support (Project AYA2006-15648-C02-01). P.G.-S. is also indebted to ‘Factoría de Cristalización’ (Consolider-Ingenio 2010). A.-N.A. is grateful to the University of Barcelona for an APIF pre-doctoral fellowship.

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Y1 - 2009/6/19

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/67649397419

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ER -

Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde

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