A Novel Chiral Super-Lewis Acidic Catalyst for Enantioselective Synthesis

Hayashi, Yujiro; Rohde, Jeffrey J.; Corey, E. J.

doi:10.1021/ja960766s

Cited by 245 publications

(150 citation statements)

References 9 publications

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“…General synthesis of the polydentate ligands (6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Reagents and conditions: a) piperidine, HOAc, EtOH, reflux, 12 h; b) secondary amine, water, r.t., catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…One important result of this study was a straightforward synthesis of ten novel 2-(aryl-disubstituted amino-1-ylmethyl)-malonic acid diethyl esters (6)(7)(8)(9)(10)(11)(12)(13)(14)(15), which constitute a functionalized class of polydentate ligands. Despite prolonged reaction times, this aza-Michael protocol led to higher yields in an aqueous medium at room temperature, and consequently, would appear to be a simple and useful synthetic protocol.…”

Section: Discussionmentioning

confidence: 99%

“…9 For preparation of such polydentate ligands, the aza-Michael reactions appear to be the key-step leading the expected b-amino esters adducts. 10 In fact, this kind of reaction has been widely employed to generate structurally diverse b-amino dicarbonyl compounds, where the undoubted importance of the aza-Michael step can be seen from the large number of unconventional methodologies, as well as the broad range of applications. 11 Most of these unconventional methodologies have used Lewis acids, which although leading to satisfactory yields, require to remove the Lewis acids through tediously chromatography.…”

Section: Introductionmentioning

confidence: 99%

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An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction

Meskini¹,

Toupet²,

Daoudi³

et al. 2010

J. Braz. Chem. Soc.

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Compostos b-amino-dicarbonilados constituem uma classe de ligantes promissores para a química de coordenação. Diante desta perspectiva, um método eficiente e fácil visando à síntese de compostos b-amino-dicarbonilados foi desenvolvido, explorando a reação de adição do tipo azo-Michael em meio aquoso. Com isso, uma série de dez dietil 2-(feniletil)malonatos dissubstituídos foram obtidos de uma maneira regiosseletiva e facilmente purificados, levando à rendimentos satisfatórios. As análises cristalográficas de dois destes compostos forneceram as informações apropriadas sobre a conformação e configuração dos mesmos. Por último, uma proposta complementar do mecanismo reacional para as reações de adição de Michael em meio aquoso foi também descrito.b-Amino dicarbonyl compounds comprise a class of useful ligands on the coordination chemistry. In view of their importance, an efficient and facile method for the synthesis of b-amino dicarbonyl compounds has been developed, exploring the aza-Michael addition reactions in an aqueous medium. It was possible to achieve good to excellent yields, along with regioselectivity, the substituted diethyl 2-(phenylmethyl)malonates that were easily isolated without any chromatographic purification. The correct configuration of two of these b-amino dicarbonyl compounds were confirmed by X-ray crystallography. A complementary mechanism of this azaMichael protocol is proposed to explain the results obtained. Keywords: polydentate ligands, b-amino dicarbonyl compounds, Michael addition, aqueous medium IntroductionThe rational design of new HIV-1 Integrase (HI) inhibitors, a valid target for chemotherapeutic intervention, 1 is primarily based on intermolecular coordination between HI / chemical inhibitor / metals (Mg 2+ and Mn 2+ , co-factors of the HI), leading to the formation of bimetallic complexes. 2,3 A number of bimetallic metal complexes, in many cases exploring the well-known polydentate ligands, appear therefore in this context to be the most promising drug candidates to HI inhibitors. 4,5 Another interesting application for such polydentate ligands involves the synergic water activation that occurs by way of the so-called 'remote metallic atoms'. Such organometallic An Efficient Protocol for Accessing b-Amino Dicarbonyl Compounds J. Braz. Chem. Soc. 1130 compounds are considered in structural terms to block the intramolecular electron transfer on the HI structure. 6 This explanation clearly demonstrates that polydentate ligands are of special interest in the field of bioorganometallic chemistry. 7 In view of our interest in designing novel bimetallic coordinating ligands 8 endowed with potential action to inhibit the HI enzyme, the object of this study is the synthesis of polydentate ligands with the same topology, as drawn in Figure 1. 9 For preparation of such polydentate ligands, the aza-Michael reactions appear to be the key-step leading the expected b-amino esters adducts. 10 In fact, this kind of reaction has been widely employed to generate structurally diverse b-amin...

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction

Meskini¹,

Toupet²,

Daoudi³

et al. 2010

J. Braz. Chem. Soc.

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show abstract

“…Aza-Michael reaction products such as β-amino esters/ketones/nitriles are useful synthons for the preparation of several nitrogen containing bioactive natural products [2], antibiotics [3], and chiral auxiliaries [4]. Because a large number of biologically active compounds contain β-aminoketone or ester moiety [5], the development of novel methodologies for the preparation of these compounds is an attractive area of research in synthetic organic chemistry.…”

Section: Introductionmentioning

confidence: 99%

LiClO4 CATALYZED AZA-MICHAEL ADDITION OF SECONDARY AMINES TO α,β-UNSATURATED ESTERS UNDER A SOLVENT-FREE CONDITION

Duc

2018

JST

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“…15 In this field, recently, many attentions have been focused on the aza-Michael reaction for the construction of valuable compounds such as β-amino carbonyl compounds 16 which are attractive precursors in preparation of a variety of biologically important natural products, antibiotics, β-amino alcohols, and chairal auxiliaries. [17][18][19][20][21][22] In contrast to the various aza-Micheal addition methods, there are few examples of the addition of amides and their analogs, due to their low reactivity, to α,β-unsaturated systems. Neutral amides have very restricted nucleophilicity but under strong basic conditions, nitrogen anions derived from them can take part in Michael-type additions to α,β-unsaturated compounds.…”

Section: Introductionmentioning

confidence: 99%

SOLVENT-FREE MICROWAVE MICHAEL ADDITION OF ISATIN AND ANILINE SCHIFF BASE OF ISATIN TO Α,β-Unsaturated ESTERS

Imanzadeh

Aghaalizadeh

Zamanloo

et al. 2011

J. Chil. Chem. Soc.

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The rapid, simple, microwave-assisted Michael addition of isatin and aniline Schiff base of isatin to a wide variety of alkyl and aryl acrylates in the presence of, tetrabutylammonium bromide (TBAB) and 1,4-diazabicyclo[2.2.2]octane (DABCO), under solvent-free conditions, is presented. Under these conditions the addition of isatin to some of alkyl and aryl acrylates afford both related Baylis-Hillman adducts as minor products and the corresponding Michael adducts as major products. Addition of isatin to ethyl acrylate leads to produce Baylis-Hillman/Michael adduct in good yield. This system dose not work on Michael acceptors of methyl acrylate and methyl methacrylate.

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A Novel Chiral Super-Lewis Acidic Catalyst for Enantioselective Synthesis

Cited by 245 publications

References 9 publications

An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction

An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction

LiClO4 CATALYZED AZA-MICHAEL ADDITION OF SECONDARY AMINES TO α,β-UNSATURATED ESTERS UNDER A SOLVENT-FREE CONDITION

SOLVENT-FREE MICROWAVE MICHAEL ADDITION OF ISATIN AND ANILINE SCHIFF BASE OF ISATIN TO Α,β-Unsaturated ESTERS

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