Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective
Nucleophilic addition to carbonyl groups is one of the most important reactions in organic synthesis. In the case of a prochiral carbonyl group, the preference for the addition of a nucleophile to one face of the ${\pi }$ system leads to unequal amounts of the two possible diastereoisomers. The mech...
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Académie des sciences
2024-03-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.298/ |
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| author | Eisenstein, Odile |
| author_facet | Eisenstein, Odile |
| author_sort | Eisenstein, Odile |
| collection | DOAJ |
| description | Nucleophilic addition to carbonyl groups is one of the most important reactions in organic synthesis. In the case of a prochiral carbonyl group, the preference for the addition of a nucleophile to one face of the ${\pi }$ system leads to unequal amounts of the two possible diastereoisomers. The mechanism of this reaction for various nucleophiles (especially the early main group hydride and the Grignard reagents) and the various noncyclic and cyclic aldehydes or ketones has fascinated computational chemists for nearly 40 years. This article describes the research that has been done on this topic, the incentive for the present author being that she started her research with this topic and is returning to it in recent years. |
| format | Article |
| id | doaj-art-dd4f98a439a440eaa6134fadfa2c7545 |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2024-03-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-dd4f98a439a440eaa6134fadfa2c75452025-02-07T13:40:29ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432024-03-0127S251910.5802/crchim.29810.5802/crchim.298Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspectiveEisenstein, Odile0https://orcid.org/0000-0001-5056-0311Department of Chemistry and Hylleraas Center for Quantum Molecular Science 0315 University of Oslo, Norway; ICGM Université de Montpellier, CNRS, ENSCM, Montpellier, FranceNucleophilic addition to carbonyl groups is one of the most important reactions in organic synthesis. In the case of a prochiral carbonyl group, the preference for the addition of a nucleophile to one face of the ${\pi }$ system leads to unequal amounts of the two possible diastereoisomers. The mechanism of this reaction for various nucleophiles (especially the early main group hydride and the Grignard reagents) and the various noncyclic and cyclic aldehydes or ketones has fascinated computational chemists for nearly 40 years. This article describes the research that has been done on this topic, the incentive for the present author being that she started her research with this topic and is returning to it in recent years.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.298/Reaction mechanismStereochemistryNucleophileCarbonylComputational chemistryAnalysis of intramolecular interactions |
| spellingShingle | Eisenstein, Odile Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective Comptes Rendus. Chimie Reaction mechanism Stereochemistry Nucleophile Carbonyl Computational chemistry Analysis of intramolecular interactions |
| title | Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective |
| title_full | Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective |
| title_fullStr | Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective |
| title_full_unstemmed | Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective |
| title_short | Nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies. A historical perspective |
| title_sort | nucleophilic addition to carbonyl groups from qualitative to quantitative computational studies a historical perspective |
| topic | Reaction mechanism Stereochemistry Nucleophile Carbonyl Computational chemistry Analysis of intramolecular interactions |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.298/ |
| work_keys_str_mv | AT eisensteinodile nucleophilicadditiontocarbonylgroupsfromqualitativetoquantitativecomputationalstudiesahistoricalperspective |