Triazole‐Gold‐Promoted, Effective Synthesis of Enones from Propargylic Esters and Alcohols: A Catalyst Offering Chemoselectivity, Acidity and Ligand Economy

Wang, Dawei; Zhang, Yanwei; Harris, Alexandria; Gautam, Lekh Nath S.; Chen, Yunfeng; Shi, Xiaodong

doi:10.1002/adsc.201100314

Cited by 64 publications

(26 citation statements)

References 58 publications

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“…The first reaction involved the synthesis of a 16-Benzylidene-3-hydroxy-steroid17-one (2); it is noteworthy that several enone derivatives have developed using some reagents such as N-bromosuccinamide [18], L-tartaric acid [19], PPh 3 AuNTf 2 [20], (IPr)AuCl]/AgBF 4 [21], diethyl acetal [22]. In this investigation, the compound 2 was prepared from estrone and benzaldehyde in basic conditions (Figure 1).…”

Section: Preparation Of An Enone-steroid Derivativementioning

confidence: 99%

Synthesis of new azaindeno-acetonitrile derivative with inotropic activity against heart failure model

2019

Biointerface Res Appl Chem

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Several steroid derivatives have prepared as inotropic drugs; however, there are few reports on azaindeno-steroid derivatives with inotropic activity. The objective of this investigation was to prepare some azaindeno-acetonitrile derivatives (compounds 3 to 7) to evaluate their biological activity on left ventricular pressure. The first step was achieved by preparation of azaindeno-steroid derivatives using reactions of etherification and addition. The second stage involves the evaluation of biological activity from azaindeno-steroid derivatives on left ventricular pressure in a heart failure model using either estrone or an enone-steroid derivative (compound 2) as controls. The results showed that only compound 6 increases left ventricular pressure compared with estrone, compounds 2-5 and 6. In conclusion, the positive inotropic effect exerted by compound 6 depends on the functional groups involved in its chemical structure.

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Section: Preparation Of An Enone-steroid Derivativementioning

confidence: 99%

Synthesis of new azaindeno-acetonitrile derivative with inotropic activity against heart failure model

2019

Biointerface Res Appl Chem

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“…It is very disappointed that the hydration product was found only with low yield ( Table 1, Entry 1). Based on our previous results on Au(I), 14 we firstly examined the effect of solvents on the reactivity using TriaAuCl 2 as the catalyst. As shown in Table 1, the reaction was strongly solvent-dependent.…”

Section: A R T Ic Le In Fo Abstract Tetrahedron Lettersmentioning

confidence: 99%

Triazole acetyl gold(III) catalyzed Meyer–Schuster rearrangement of propargyl alcohols

Yang

Shen

Wang

et al. 2016

Tetrahedron Letters

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A new type triazole acetyl gold(III) was prepared and found to be an effective catalyst in Meyer-Schuster rearrangement of propargyl alcohols. The reactions proceeded well under much milder conditions to afford enones bearing a wide range of functional groups, thereby opening a new avenue for gold(III) catalysis. In addition, TriaAuCl 2 catalyst was also effective on promotion of ahaloenones synthesis.

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“…Whilst there are numerous reports of the Au-catalyzed Meyer-Schuster rearrangement of propargylic alcohols [44][45][46][47][48][49], many of these reactions are carried out in MeOH as solvent and require heating for prolonged periods. Under our optimized conditions, the rearrangement of a wide range of propargylic alcohols 46 could be achieved at room temperature using 2 mol % Au catalyst in toluene, in the presence of either 20 mol % of boronic acid 43 or 1 equiv of MeOH as an additive (Scheme 11) [43,50].…”

Section: Gold-catalyzed Reaction Of Boronic Acids With Propargylic Almentioning

confidence: 99%

Complexity-generating hydration reactions via gold-catalyzed addition of boronic acids to alkynes

Sheppard

2012

Pure and Applied Chemistry

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Boronic acids can serve as organic soluble substitutes for water molecules in the metal-catalyzed hydration of alkynes. The Au-catalyzed addition of boronic acids to alkynes provides an alternative method for enolate generation, which proceeds under exceptionally mild conditions. The resulting enolates can be trapped by aldehydes present in the reaction mixture, giving aldol products that can be isolated as cyclic borate esters. These compounds are versatile synthetic intermediates that can be elaborated into a variety of products by transformation of the boron moiety. The Au-catalyzed reaction of boronic acids with propargylic alcohols results in efficient Meyer–Schuster rearrangement to the corresponding enones. The rearrangement of tertiary alcohols gives (E)-enones with moderate to good selectivity, and the addition of a boronic acid to the reaction appears to enhance the level of geometrical control. The rearrangement of primary alcohols to terminal enones also occurs readily in the presence of catalytic Au(I) and a boronic acid, and the resulting terminal enones can be reacted with nucleophiles in one-pot procedures to give a variety of β-substituted ketones.

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Triazole‐Gold‐Promoted, Effective Synthesis of Enones from Propargylic Esters and Alcohols: A Catalyst Offering Chemoselectivity, Acidity and Ligand Economy

Cited by 64 publications

References 58 publications

Synthesis of new azaindeno-acetonitrile derivative with inotropic activity against heart failure model

Synthesis of new azaindeno-acetonitrile derivative with inotropic activity against heart failure model

Triazole acetyl gold(III) catalyzed Meyer–Schuster rearrangement of propargyl alcohols

Complexity-generating hydration reactions via gold-catalyzed addition of boronic acids to alkynes

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