Studies on the transition metal-catalyzed synthesis of variously substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones

Rossi, Renzo; Bellina, Fabio; Bechini, Chiara; Mannina, Luisa; Vergamini, Piergiorgio

doi:10.1016/s0040-4020(97)10265-4

Cited by 100 publications

(34 citation statements)

References 38 publications

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“…It is known from previously published studies 23 that substituents at the exocyclic multiple bond of dipolarophiles have trans configuration, which together with stereochemistry at spiro atom C-2 suggests coordinated endo cycloaddition 21 (Scheme 3).…”

mentioning

confidence: 99%

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Anis’kov

Kamneva

Zheleznova

et al. 2015

Chem Heterocycl Comp

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mentioning

confidence: 99%

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Anis’kov

Kamneva

Zheleznova

et al. 2015

Chem Heterocycl Comp

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“…Although no rigorous comparison has been made, the available data suggest that the alkynylzincbased procedure favorably compares with that based on the Sonogashira protocol. Although different from the reaction discussed here, another recent application of the Pd-catalyzed cross-coupling with alkynylzincs [22b,c, 163, 296] for the α-alkynylation of α-bromo-α,β-unsaturated esters [301] also points to the superior reactivity of alkynylzincs in the Pd-catalyzed cross-coupling.…”

Section: Pd-catalyzed α-Alkynylation Of Carbonyl Compoundsmentioning

confidence: 62%

Pd‐Catalyzed Cross‐Coupling with Organometals Containing Zn, Al, Zr, and so on – The Negishi Coupling and Its Recent Advances

Kamada

Kim

et al. 2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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The Pd-or Ni-catalyzed cross-coupling reactions of organometals containing Zn, Al, Zr, and B as well as related reactions of those containing Mg and several other metals collectively have emerged as arguably the most widely applicable organic skeleton construction method discovered and developed over the past several decades, allowing synthetic chemists to prepare practically all types of organic compounds. In this chapter, some of the seminal and critically important discoveries and early developments in the 1970s as well as their current scope are briefly discussed. Some of the notable discoveries and developments include (i) identification of superior properties of Pd as a critical element for crosscoupling relative to Ni, (ii) the broad scope of Pd-or Ni-catalyzed cross-coupling with respect to metal countercations including Zn, Al, Zr, B, and Mg, (iii) the hydrometallation-Pd-catalyzed cross-coupling sequential processes for selective syntheses of alkenes, dienes, oligoenes, and oligoenynes, (iv) double metal catalysis involving Pd or Ni and added metal compounds containing Zn, In, Li, and others, and (v) realization of high turnover numbers (TONs) (≥10 3 -10 9 ) through the use of chelating phosphines, such as bis-[2-(diphenylphosphino)phenyl] ether (DPEphos) and 1,1 -Bis(diphenylphosphino)ferrocene (dppf).The Zr-catalyzed alkyne carboalumination and the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction) have provided efficient and selective routes to (E)-trisubstituted alkenylalanes and 2-substituted chiral alkylalanes, respectively. These reactions provide two additional examples of prototypical transition metal-catalyzed organometallic reactions. Significantly, they can be readily combined with the Pd-or Ni-catalyzed cross-coupling for the synthesis of trisubstituted alkenes embracing a wide variety of natural products, such as terpenoids, carotenoids, and others, as well as various chiral organics including deoxypolypropionates and saturated terpenoids. The Zr-catalyzed alkyne carboalumination has been applied to the synthesis of a large number (>100) of natural products, while the ZACA reaction has been transformed from a mere scientific novelty to a full-fledged asymmetric synthetic method that is catalytic in both transition metal (Zr) and chiral auxiliaries through a series of breakthroughs.

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“…In recent years, there has been a great interest in preparing butenolides [1][2][3][4][5][6][7][8] containing compounds due to the biological effects attributed to this class of natural products such as freelingyne, rubrolides, etrenolin-furanosesquiterpenoid, Protoanemonin [9][10][11]. Among these bioactive compounds, there exist the alkylidenes butenolides, which have a large spectrum of biological activity [12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some Butenolides and Study of their Antibacterial Activity

Tamma

Gherraf

2013

ILCPA

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Butenolides and their analogues represent a wide range of natural compounds of a medical and biological importance. In the last decades, a great number of compounds of various structures, in general from Alkylidene butenolide, were isolated and showed biological activities. In this work we have studied the reactivity of some alkylidene butenolide and their antibacterial activity. the study is of a scientific interest in terms of the synthesis of new compounds (Butenolide 01: 5-hydroxy-5-(1-methoxypropan-2-yl)-4-methylfuran-2(5H)-one, Butenolide 02:5-(1-methoxypropan-2-yl)-4-methylfuran-2(5H)-one) that have not been studied before by other researchers; and of an economic importance because of its synthesis process which is easy and inexpensive. Moreover, butenolide showed a positive antimicrobial activity (antibiotic) against pathogenic bacteria (mainly Enterobacter hafniae).

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Studies on the transition metal-catalyzed synthesis of variously substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones

Cited by 100 publications

References 38 publications

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Pd‐Catalyzed Cross‐Coupling with Organometals Containing Zn, Al, Zr, and so on – The Negishi Coupling and Its Recent Advances

Synthesis of some Butenolides and Study of their Antibacterial Activity

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