Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters

PraveenGanesh, Nageswaran; Candia, Cristina de; Memboeuf, Antony; Lendvay, György; Gimbert, Yves; Chavant, Pierre Y.

doi:10.1016/j.jorganchem.2010.07.009

Cited by 7 publications

(3 citation statements)

References 34 publications

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“…Our continued interest in the preparation and reactivity of nitrones led us to the design of the chiral cyclic nitrone 1 (MiPNO; Figure ) as a versatile precursor of α-amino acids . MiPNO is conveniently stable to heat, and we assumed that it could be a worthy substrate for the study of direct coupling reactions with aromatic halides.…”

Section: Introductionmentioning

confidence: 99%

Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters

et al. 2012

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Cocatalysis by pivalic acid or copper bromide allows a very fast, clean, and high-yielding palladium-catalyzed coupling of a large array of aryl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO. The study of the reaction conditions, scope, and mechanism is presented. Applied to the chiral nitrone MiPNO, this transformation provides a straightforward access to enantiopure α-methyl α-arylglycine esters.

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Section: Introductionmentioning

confidence: 99%

Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters

et al. 2012

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“…Among boronic acid derivatives, arylboronic hexylene glycol esters emerged as interesting compounds. Murata’s team and ours have shown that they exhibit excellent stability toward air, water, and chromatography, and undergo Suzuki−Miyaura reactions with aryl iodides, bromides, and triflates in excellent yields. Advantageously, hexylene glycola solventis much less expensive than pinacol .…”

Section: Introductionmentioning

confidence: 85%

Noncryogenic Preparation of Functionalized Arylboronic Esters through a Magnesium−Iodine Exchange with in Situ Quench

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Einhorn

et al. 2011

Org. Process Res. Dev.

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Various functionalized aryl boronic esters derived from hexylene glycol and pinacol were prepared in excellent yields according to a simple, safe procedure. The metal-halogen exchange reaction between i PrMgCl 3 LiCl and aryl iodides is performed at 0 °C in the presence of a cyclic borate ester (MPBO i Pr or PinBO i Pr); the organomagnesium intermediate is immediately trapped in situ so that no accumulation of hazardous reactive species can occur. The reaction is very selective, and particularly clean crude products are obtained. The scope of the procedure and the tuning of reaction parameters are investigated.

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“…Unfortunately, the desired product was obtained in only 31% yield (Table , entry 1). Then we decided to examine the alternative vinylboronic esters under these conditions. After a series of reaction optimizations, we ultimately found the optimal conditions to be the use of 3 equiv of dimethylzinc in DMF at 60 °C (Table , entry 4), which signicantly facilitated this tandem transformation to afford the desired product in 85% yield.…”

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confidence: 99%

Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction

et al. 2016

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A general and efficient synthesis of the 2H-tetrahydro-4,6-dioxo-1,2-oxazine ring system through a tandem nucleophilic addition and transesterification reaction is described. The reaction is highly functional-group-tolerant and proceeds under mild conditions, affording the corresponding products in good to excellent yields. This method represents the first general synthetic route to access this heterocyclic scaffold, which exists in the complex natural products alchivemycin A and B with significant antibiotic activities.

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Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters

Cited by 7 publications

References 34 publications

Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters

Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters

Noncryogenic Preparation of Functionalized Arylboronic Esters through a Magnesium−Iodine Exchange with in Situ Quench

Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction

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