Diastereoselective addition of nitro compounds to α,β-unsaturated γ-butyrolactones

Rosso, Giovanni; Pilli, Ronaldo A.

doi:10.1016/j.tetlet.2005.10.163

Cited by 18 publications

(9 citation statements)

References 24 publications

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“…[132] This basic reagent is also able to promote the Michael addition of nitroalkanes to a,b-usaturated compounds, [15] so that at andemc onjugate addition-Nef reactiono fg-nitro ester 177 to butenolides 176 leading to substituted lactones 178 can be envisaged (Scheme 61). [133] This transformation can also be carriedo ut in two separates teps using 0.1 equivalent of DBUf or the conjugate addition followed by the Nefr eaction using KMnO 4 -SiO 2 ,but the overall chemical yield is considerably lower (27% for each example).…”

Section: O Ther Methodsmentioning

confidence: 99%

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

2015

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This review article reports new procedures and practical application of the nitro to carbonyl conversion that appeared in the literature after our\ud comprehensive report published in 2004. Beside traditional and well explored reactant systems, new procedures including the utilization of molecular oxygen and photoredox catalysis have been introduced for the Nef reaction. Of notable interest is the utilizationof the nitro to carbonyl conversion in tandem and cascade processes aimed at the preparation of hetero and carbocyclic derivatives

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Section: O Ther Methodsmentioning

confidence: 99%

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

2015

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“…(1)] have been widely explored and exploited for many polyfunctional targets. [4][5][6][7][8][9][10] Strong bases such as tetramethylguanidine (TMG), [11,12] DBU, [13][14][15][16][17][18] benzyltrimethylammonium hydroxide (Triton B [19][20][21] ) or NaOH [22] are usually required to generate the nucleophilic species. However, "activated" nitro compounds [Eq.…”

Section: Introductionmentioning

confidence: 99%

Michael Additions versus Cycloaddition Condensations with Ethyl Nitroacetate and Electron‐Deficient Olefins

Trogu

Sarlo

Machetti

2009

Chemistry A European J

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Ethyl nitroacetate (1) reacts with electron-poor olefins in the presence of a base to give either the Michael adducts 3 or the isoxazoline cycloadducts 4, resulting from water elimination. The proportions of the two products depend on the reaction conditions and change in the course of the process. Kinetic profiles for the two reactions show that the cycloaddition-condensations require long induction times that dramatically decrease upon addition of a copper salt to the catalytic system: the drops in the induction time cause increases in the proportion of cycloadducts 4, which are often the sole reaction products. This is the first report on the selective formation of products 3 and 4 from primary nitro compounds through modulation of the catalytic system.

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“…The 5‐substituted furanones 19 and 20 were initially employed as Michael acceptors in the reaction with nitromethane to explore the diastereoselection of the reaction [16] . Treatment of 19 with DBU (10 mol%) at room temperature, allowed the isolation of trans ‐γ‐butyrolactone 21 , in 88 % yield, while 22 was isolated in 93 % yield from 20 , under the same reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Formal Syntheses of (±)‐Tuberostemospiroline and (±)‐Stemona‐lactam R and Total Synthesis of (±)‐Stemoamide

2022

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The structure proposed for the putative Stemona alkaloid named as parvistemoamide (4 a or 4 b) has been questioned after revising the literature data and an attempted preparation of structure 4 a, which led to a 5 : 1 mixture of (±)‐stemoamide (1). Studies on the intramolecular Friedel‐Crafts alkylation of a furan 12 containing a Z double bond tethered to a precursor of a N‐acyliminium ion are reported. As shown for bromo substituted furan 31, the cyclization occurred when a 4‐carbon saturated tether was present, allowing for the formal syntheses of racemic tuberostemospiroline (2) and stemona‐lactam R (3).

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Diastereoselective addition of nitro compounds to α,β-unsaturated γ-butyrolactones

Cited by 18 publications

References 24 publications

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

Michael Additions versus Cycloaddition Condensations with Ethyl Nitroacetate and Electron‐Deficient Olefins

Formal Syntheses of (±)‐Tuberostemospiroline and (±)‐Stemona‐lactam R and Total Synthesis of (±)‐Stemoamide

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