Generation of chiral N-acylpyridinium ions by means of silyl triflates and their diastereoselective trapping reactions: formation of N-acyldihydropyridines and N-acyldihydropyridones

Hoesl, Cornelia E.; Maurus, Markus; Pabel, Jörg; Polborn, Kurt; Wanner, Klaus T.

doi:10.1016/s0040-4020(02)00675-0

Cited by 32 publications

(14 citation statements)

References 22 publications

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“…Furthermore, stereoselective variants have been reported. Comins, 9 Wanner, 10 and Charette 11 have pioneered the use of chiral auxiliaries to control the facial selectivity of Grignard additions to pyridinium salts, though a blocking group at the C3 position is often required for high regio- and diastereoselectivity.…”

Section: Introductionmentioning

confidence: 99%

Nickel-catalyzed enantioselective arylation of pyridine

2016

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We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridiniumions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

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Section: Introductionmentioning

confidence: 99%

Nickel-catalyzed enantioselective arylation of pyridine

2016

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“…We attributed the moderate yield to incomplete conversion of 1 under these reaction conditions. Consistent with this idea, a higher yield of 72% was obtained by increasing the loading of both i -PrCOCl and EtMgBr to 4.0 equiv (entry 3), although this also decreased regioselectivity slightly to 78:7:15. The reaction temperature strongly affected regioselectivity, with higher temperatures leading to lower 1,6-regioselectivity (entries 3–5).…”

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confidence: 56%

Regioselective Nucleophilic Addition of Organometallic Reagents to 3-Geminal Bis(silyl) N-Acyl Pyridinium

et al. 2014

Org. Lett.

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A regioselective nucleophilic addition to 3-geminal bis(silyl) N-acyl pyridinium has been described. Geminal bis(silane) shows contrasting roles that lead to different regioselectivities for the addition of different nucleophiles: its steric effect dominates to favor 1,6-addition of alkyl, vinyl, and aryl organometallic reagents; its directing effect dominates to favor 1,2-addition of less sterically demanding alkynyl Grignard reagents.

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“…Some acyl pyridinium salts such as 180 can be obtained in good to excellent yields by treatment of pyridines 178 with acid chloride 179 (Scheme 16.48) [151].…”

Section: Reactions With Acyl Halides and Related Compoundsmentioning

confidence: 99%

Six‐Membered Heterocycles: Pyridines

González‐Bello

Castedo

2011

Modern Heterocyclic Chemistry

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Figure 16.5 Examples of agrochemical pyridine derivatives and their applications.1434j 16 Six-Membered Heterocycles: Pyridines IR DataThe pyridine IR spectrum is quite similar to the corresponding vibrations of benzene. Pyridine has C-H stretching frequencies in the range 3020-3070 cm À1 as well as C¼C and C¼N stretching frequencies at 1590-1660 cm À1 and near 1500 cm À1 . N J 2,3 = 4-6 J 2,4 = 0-2.5 J 2,5 = 0-2.5 2 3 4 5 6 J 2,6 = 0-0.6 J 3,4 = 7-9 J 3,5 = 0.5-2 1436j 16 Six-Membered Heterocycles: Pyridines R + Metal catalyst ∆ R = alkyl, vinyl, aryl Scheme 16.2 16.

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Generation of chiral N-acylpyridinium ions by means of silyl triflates and their diastereoselective trapping reactions: formation of N-acyldihydropyridines and N-acyldihydropyridones

Cited by 32 publications

References 22 publications

Nickel-catalyzed enantioselective arylation of pyridine

Nickel-catalyzed enantioselective arylation of pyridine

Regioselective Nucleophilic Addition of Organometallic Reagents to 3-Geminal Bis(silyl) N-Acyl Pyridinium

Six‐Membered Heterocycles: Pyridines

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