Photochemical reactivity of aldimines from 2,2-dimethyl-3-oxo-3-phenylpropanal

Armesto, Diego; Ramos, Ana; Perez‐Ossorio, R.; Horspool, W. M.

doi:10.1039/p19860000091

Cited by 6 publications

(1 citation statement)

References 3 publications

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“…[147] N-Aryl Ketimines; General Procedure: [141] To a mixture of a ketone (0.10 mol) and an aromatic amine (0.12 mol) in benzene (CAU- Magnesium sulfate is often used as a drying agent and as a Lewis acid in aldimine syntheses. This way functionalized imines such as N-benzyl-AE-chloro aldimines, [148] â-chloro aldimines, [129] N-benzyl-N-(5-chloro-2,2-dimethylpentylidene)amine, [149] AE,â-unsaturated aldimines, [150] and â-oxo aldehydes, [151] as well as imines such as cyclopropanecarbaldimines, [152] N-benzylidene-N-homoallylamines, [153] and simple aliphatic aldimines, [154][155][156][157] are available. Alkylammonium salts can also be condensed this way, provided that 1 equivalent of triethylamine is added to the reaction mixture.…”

Section: Nhr 3 Homentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Compounds with the general structure R 1 R 2 C=NR 3 , referred to as imines, were first obtained by Schiff via condensation of ketones and aldehydes with primary amines. Therefore, the condensation products are also called Schiff bases. In addition, the nominations azomethine, ketimine (derived from ketones), aldimine (derived from aldehydes), and anil (derived from anilines) are in use. It is recommended that the terms imine(s), ketimine(s), or aldimine(s) are used, rather than Schiff base(s) or azomethine(s).Since imines have to be considered as analogues of carbonyl compounds, many of the chemical properties are similar to the latter. Imines are used in new C-C bond formations, and reactions with electrophiles (e.g., aldehydes, alkyl halides), and the C=N moiety can undergo nucleophilic reactions. Generally, imines are very useful compounds in organic synthesis, as they are used in several syntheses of aza-heterocyclic compounds. Most imines are stable in an alkaline medium and therefore can be dried over potassium hydroxide. In diluted acid, however, they are easily hydrolyzed. In many cases intermediary imines cannot be isolated because of their lability. The presence of a C=N bond creates the possibility for E/Z isomerism (syn/anti). It has been recognized that such geomet-

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Section: Nhr 3 Homentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Catalytic β‐Boration/Oxidation of 1‐Azadienes

Solé¹,

Fernández²

2009

Chemistry An Asian Journal

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Catalytic 1,3‐Difunctionalisation of Organic Backbones through a Highly Stereoselective, One‐Pot, Boron Conjugate‐Addition/Reduction/Oxidation Process

Solé

Tatla

Mata

et al. 2011

Chemistry A European J

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A simple one-pot, three-step synthetic route to chiral 1,3-amino alcohols and 1,3-diols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is an enantioselective β-boration of α,β-unsaturated imines and ketones, respectively. The enantioselectivity provided by the Cu(I) catalyst modified with Josiphos- and Mandyphos-type ligands has been examined. The oxidative substitution of the boryl unit with a hydroxyl group proceeds with complete retention of configuration at the C(β)-atom. In parallel, the stoichiometric reduction of the imino or carbonyl group provides a second stereogenic centre. Depending on the nature of the reducing reagent, exceptionally high diastereoselectivity is achieved, especially for syn-1,3-amino alcohols and 1,3-diols.

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Photochemical reactivity of aldimines from 2,2-dimethyl-3-oxo-3-phenylpropanal

Cited by 6 publications

References 3 publications

Product Class 7: Imines

Product Class 7: Imines

Catalytic β‐Boration/Oxidation of 1‐Azadienes

Catalytic 1,3‐Difunctionalisation of Organic Backbones through a Highly Stereoselective, One‐Pot, Boron Conjugate‐Addition/Reduction/Oxidation Process

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