The Mannich Reaction Involving Optically Active Substituted Mandelic Acids and Nitroalkanes<sup>1,2</sup>

Grillot, Gerald F.; Bashford, Raymond I.

doi:10.1021/ja01156a029

Cited by 11 publications

(2 citation statements)

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“…Grillot and Bashford later used Johnson's procedures during their investigations into Mannich reactions of optically active nitroalkanes. 39 Lambert and Rose investigated the use of this chemistry for selective monoaddition of aminomethanols to nitroethane, which typically undergoes double addition. They successfully performed the monoaddition reaction of diethylaminomethanol with nitroethane (Scheme 11).…”

Section: First Reportsmentioning

confidence: 99%

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Nitro-Mannich Reaction

2013

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Section: First Reportsmentioning

confidence: 99%

“…Products were also reduced to the corresponding polyamines in 23–95% yield by hydrogenation over RaNi. Grillot and Bashford later used Johnson’s procedures during their investigations into Mannich reactions of optically active nitroalkanes …”

Section: Early Developmentsmentioning

confidence: 99%

Nitro-Mannich Reaction

2013

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Mannich Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is a multicomponent condensation between an amine, an enolizable carbonyl compound (donor), and a nonenolizable carbonyl compound (acceptor) to form a β‐amino carbonyl compound (ketone or ester), with the concomitant formation of both carbon‐carbon and carbon‐nitrogen bonds and is known as the Mannich reaction, or Mannich condensation. Several variants of this reaction have been discussed. The Mannich reaction occurs under very simple conditions and gives desired compounds in high yields with two potential chiral centers. This reaction has been extensively modified beside the variant reactions. Several conditions of this reaction have been discussed to enhance stereoselectivity as well as the final yield. This reaction has been used for the preparation of stereoselective compounds under catalytic conditions.

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Aminomethylierung. Eine Studie zur Aufklärung und Einordnung der Mannich‐Reaktion

Hellmann¹,

Opitz²

1956

Angewandte Chemie

113

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Fur den Mechanismus d e r Mannich-Reaktion wird die beherrschende Rolle des mesomeren Aminomethyl-(carbeniurn-imonium)-Ions als aminomethylierendes Agens herausgestellt. Mannich-Kondensation und Transamino-methylierung lassen sich als Spezialfalle in den Rahmen des umfassenderen Reaktionstypus d e r Aminomethylierung einordnen. Es wird gezeigt, daO dieser Reaktion prinzipiell alle nucleophilen Verbindungen zuganglich sind. Die Reaktionsmechanismen d e r Aminomethylierung, je nach Wahl d e r Komponenten und Bedingungen, werden erortert. Mannich-Reaktion als unsymmetrische KondensationAngew. Chem. 1 68. Jahrg. 1956 Nr. 8

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The Mannich Reaction Involving Optically Active Substituted Mandelic Acids and Nitroalkanes^1,2

Cited by 11 publications

References 1 publication

Nitro-Mannich Reaction

Nitro-Mannich Reaction

Mannich Reaction

Aminomethylierung. Eine Studie zur Aufklärung und Einordnung der Mannich‐Reaktion

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The Mannich Reaction Involving Optically Active Substituted Mandelic Acids and Nitroalkanes1,2

Cited by 11 publications

References 1 publication

Nitro-Mannich Reaction

Nitro-Mannich Reaction

Mannich Reaction

Aminomethylierung. Eine Studie zur Aufklärung und Einordnung der Mannich‐Reaktion

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The Mannich Reaction Involving Optically Active Substituted Mandelic Acids and Nitroalkanes^1,2