Three partners for a one pot palladium-mediated synthesis of various tetrahydrofurans

Cavicchioli, Marcello; Sixdenier, E.; Derrey, A.; Bouyssi, Didier; Balme, Geneviève

doi:10.1016/s0040-4039(97)00195-0

Cited by 32 publications

(22 citation statements)

References 8 publications

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“…[2b] The Michael addition of propargyl alcohol to ethyl 2-phenylsulfonyl cinnamate (1), [10] 3 ) n (n ϭ 1-2) is highly effective in the catalysis of this cyclization (90%), for the preparation of bulk quantities of 3 the use of CuI(PPh 3 ) n complexes (n ϭ 1-3) was preferred for economic reasons. These complexes may be prepared beforehand [11] but are just as effective when prepared in situ and they offer the advantage over CuI of increased solubility in organic solvents.…”

Section: Resultsmentioning

confidence: 99%

“…Changing the carbon ligand on zinc from an sp 2 to an sp 3 hybridised carbon results in a drastic change in the course of the reaction. When ethyl zinc chloride, prepared from ethyl magnesium bromide, is reacted with 3 under the same reaction conditions employed for aryl zinc halides, only traces of the substitution product 15 were observed.…”

Section: Resultsmentioning

confidence: 99%

“…The reactivity of organozinc halide reagents is apparently related to the hybridisation of the carbon ligand. Alkyl zinc halides where the negative charge is centred in an sp 3 hybridised orbital are more reactive nucleophiles. They are reactive enough to substitute the allylic sulfone 3 without requiring transition metal catalysis.…”

Section: Resultsmentioning

confidence: 99%

“…[2] The introduction of a third component into this synthesis would greatly enhance the diversity of products available, [3] hence a three-component synthesis of substituted 2,5-dihydrofurans was postulated (Scheme 1). Scheme …”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The Effect of the Carbon Ligand on the Reaction of Organozinc Reagents in the Synthesis of Substituted 2,5-Dihydrofurans: A Rare Example of An Uncatalysed Allylic-Substitution Reaction Involving Alkyl Zinc Halides

Woods

Monteiro

Balme³

2000

Eur. J. Org. Chem.

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Organozinc halides derived from Grignard reagents behave differently in their reaction with ethyl (±±)‐(2RS,3SR)‐tetrahydro‐4‐methylene‐2‐phenyl‐3‐(phenylsulfonyl)furan‐3‐carboxylate (3) according to the hybridisation of the carbon ligand. During the development of short multi‐component reactions for the synthesis of diverse functionalized ethyl 2,5‐dihydrofuran‐3‐carboxylates it was discovered that aryl and vinyl zinc halides undergo clean reaction with 3 in the presence of Pd(PPh3)4. In contrast, when alkyl zinc halides are reacted with 3 in the presence of Pd(PPh3)4, reductive desulfonation of 3 is observed. Remarkably, in the absence of a transition metal catalyst, the allylic substitution of 3 with alkyl zinc halides proceeds cleanly and in moderate to good yield.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Effect of the Carbon Ligand on the Reaction of Organozinc Reagents in the Synthesis of Substituted 2,5-Dihydrofurans: A Rare Example of An Uncatalysed Allylic-Substitution Reaction Involving Alkyl Zinc Halides

Woods

Monteiro

Balme³

2000

Eur. J. Org. Chem.

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“…The synthesis of highly substituted tetrahydrofurans by means of a multicomponent reaction based on this palladium-mediated cyclization process was reported by Balme and co-workers [94]. In this reaction, formation of enolate 103 by the initial 1,4-addition of an allylic alcohol to the conjugate acceptor 102 is followed by a palladium-mediated cyclization reaction involving the unsaturated halide.…”

Section: Carbonucleophilesmentioning

confidence: 97%

Metal‐Catalyzed Multicomponent Reactions

Balme

Bouyssi

Monteiro

2005

Multicomponent Reactions

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Maximizing Synthetic Efficiency: Multi-Component Transformations Lead the Way

Bienaymé¹,

Hulme

Oddon³

et al. 2000

Chem. Eur. J.

1,086

301

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With the emergence of high-throughput screening in the pharmaceutical industry in the early 1990's, organic chemists were faced with a new challenge: how to prepare large collections of molecules (the libraries) to "feed" the high-throughput screen? The unique exploratory power of some reactions (such as the 40 year-old Ugi four-component condensation) was soon recognized to be extremely valuable to produce libraries in a time- and cost-effective manner. Over the last five years, industrial and academic researchers have made these powerful transformations into one of the most efficient and cost-effective tools for combinatorial and parallel synthesis.

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Three partners for a one pot palladium-mediated synthesis of various tetrahydrofurans

Cited by 32 publications

References 8 publications

The Effect of the Carbon Ligand on the Reaction of Organozinc Reagents in the Synthesis of Substituted 2,5-Dihydrofurans: A Rare Example of An Uncatalysed Allylic-Substitution Reaction Involving Alkyl Zinc Halides

The Effect of the Carbon Ligand on the Reaction of Organozinc Reagents in the Synthesis of Substituted 2,5-Dihydrofurans: A Rare Example of An Uncatalysed Allylic-Substitution Reaction Involving Alkyl Zinc Halides

Metal‐Catalyzed Multicomponent Reactions

Maximizing Synthetic Efficiency: Multi-Component Transformations Lead the Way

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