Effects of Magnesium Salts and Amines on the Stereoselectivity in the Imine Aldol Reaction

Azaenolates are, quite simply, the aza variant of enolates. Compared to their oxygen counterparts, additional control of the reactivity of azaenolates can be achieved by altering the substituent on the nitrogen atom as well as the metal counterion. Since the seminal examples reported in the early 1960s, azaenolates of various metals have been shown to react with a diverse set of electrophilic partners, including challenging electrophiles such as alkyl fluorides, epoxides, and oxetanes. This review describes in detail the current state of the art of the chemistry of azaenolates derived from imines, with a particular focus on the comparison of the reactivity exhibited with different metal counterions.

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“…Hayashi investigated the anti/syn selectivity of this reaction with different magnesium salts in 2007. [127]…”

Section: Reaction With Aldehydes and Ketonesmentioning

confidence: 99%

“…anti Selectivity was observed in the aldol products under these conditions. Hayashi investigated the anti/syn selectivity of this reaction with different magnesium salts in 2007 [127] …”

Section: Magnesiummentioning

confidence: 99%

Imine Azaenolates: Synthesis, Reactivity, and Outlook

John‐Campbell

Sheppard

2022

Adv Synth Catal

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Aldol Reaction—Homogeneous

Cai

2011

Encyclopedia of Catalysis

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The aldol reaction is one of the oldest and important methods for the construction of carbon–carbon bonds in organic chemistry. Over the last 30 years, tremendous efforts have resulted in the development of many highly sophisticated and efficient catalytic methods of modern aldol reactions in catalytic chemo‐, regio‐, enantio‐, and diastereoselective manners. This review outlined those efforts in homogeneous catalysis and discussed with selected examples (331 publications) according to the different elemental types of catalysts, for example, transition metals and rare earth metals based Lewis acids, main group metals based catalysts, multifunctional catalysts, and metal‐free catalysts.

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Formation of Aldehydes and Ketones by Condensation Reactions

Larock

Dubrovskiy

Markina

2018

Comprehensive Organic Transformations

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Acetoacetic Ester Acyloin and Related Reactions Benzoin and Related Reactions Dieckmann and Related Reactions Mannich Michael Thorpe–Ziegler Aldol and Related Reactions Other Condensation Reactions

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Effects of Magnesium Salts and Amines on the Stereoselectivity in the Imine Aldol Reaction

Cited by 8 publications

References 15 publications

Imine Azaenolates: Synthesis, Reactivity, and Outlook

Imine Azaenolates: Synthesis, Reactivity, and Outlook

Aldol Reaction—Homogeneous

Formation of Aldehydes and Ketones by Condensation Reactions

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