Stereoselective formation of 4-substituted-1,4-dihydronicotinoyl complexes utilizing the chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]

Beckett, R.Paul; Burgess, Vicky A.; Davies, Stephen G.; Whittaker, Mark

doi:10.1016/s0040-4039(00)73651-3

Cited by 13 publications

(3 citation statements)

References 29 publications

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“…In cases with more activated pyridines containing stabilizing electron-withdrawing groups, nucleophilic addition has been proposed to occur to the uncomplexed pyridine followed by the trapping of the resulting anion. This is often considered in the case of the addition of 4-selective nucleophiles to nicotinic derivatives carrying electron-withdrawing groups at the 3-position, , although in similar examples addition to the N -acyl pyridinium salts has also been proposed.…”

Section: Nucleophilic Addition Of Organometallic Reagents To N-acyl P...mentioning

confidence: 99%

“…Davies and co-workers reported the use of an iron acyl auxiliary [η 5 -(Cp)Fe(CO)(PPh 3 )] at C-3, which gave high levels of stereoinduction due to a postulated π–π interaction involving the triphenylphosphine ligands . Complete regio- and stereoselective additions were obtained with alkyl- and aryllithium reagents.…”

Section: Nucleophilic Addition Of Organometallic Reagents To N-acyl P...mentioning

confidence: 99%

“…195,196 Davies and co-workers reported the use of an iron acyl auxiliary [η 5 -(Cp)Fe(CO)(PPh 3 )] at C-3, which gave high levels of stereoinduction due to a postulated π−π interaction involving the triphenylphosphine ligands. 34 Complete regioand stereoselective additions were obtained with alkyl-and aryllithium reagents. In the latter system the addition was proposed to occur to the pyridine prior to trapping with an acyl or alkyl electrophile in good yields.…”

Section: Diastereoselective 14-addition Controlled By Pyridine 3-subs...mentioning

confidence: 99%

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Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition toN-Activated Pyridines

et al. 2012

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Introduction 2643 2. Nucleophilic Addition of Organometallic Reagents to N-Acyl Pyridinium Salts 2644 2.1. Regioselective Additions to N-Acyl Pyridinium Species and Their Derivatives 2644 2.1.1. Influence of Pyridine Ring Substituents on Regioselectivity of Addition 2646 2.1.2. Control of Regio-and Diastereoselectivity by the Introduction of Removable Blocking Groups 2648 2.2. Synthesis of 4-Pyridones: 1,2-Addition to 4-Methoxypyridines 2649 2.2.1. Diastereoselective Addition to 3-Trialkylsilyl-4-methoxypyridines 2651 2.2.2. Application in the Synthesis of Natural Products Containing Chiral Piperidine Units 2652 2.3. Diastereoselective 1,2-Addition to N-Imidoyl Pyridinium Salts 2652 2.4. Enantioselective 1,2-Addition Controlled by a Chiral Catalyst 2657 2.5. Diastereoselective 1,4-Addition Controlled by Pyridine 3-Substituents 2657 3. Nucleophilic Addition to N-Alkyl Pyridinium Salts and Their Derivatives 2659 3.1. Regioselective Additions to N-Alkyl Pyridinium SaltsNature of the Nucleophile 2659 3.1.1. Organometallic Reagents as Nucleophiles 2659 3.1.2. Cyanide as Nucleophile 2663 3.2. Diastereoselective Additions of Organometallic Reagents to N-Alkyl Pyridinium Salts 2663 3.3. Regioselective Additions of Enolates to N-Alkyl Pyridinium Salts 2666 3.3.1. Wenkert Procedure: Seminal Work 2667 3.3.2. Wenkert Procedure: Addition of Nucleophiles Positioned at the Nitrogen of Indole Derivatives 2670 3.3.3. Wenkert Procedure: Addition of Enolates Located at the C-2/C-3 Position of Indoles 2671 3.3.4. Addition of Miscellaneous Nucleophiles to N-Alkyl Pyridinium Species 2674 4. Nucleophilic Additions to N-Heteroatom Pyridinium Species 2676 4.1. Nucleophilic Additions to Pyridine N-Oxides and N−O Salts 4.1.1. Properties, Synthesis, and Deprotection of Pyridine N-Oxides 4.1.2. Addition of Grignard Reagents to Pyridine N-Oxides 4.1.3. Addition of Cyanide Nucleophiles via Reissert-Type Reactions 4.1.4. Addition of Hetero Nucleophiles to Pyridine N-Oxides and N−O Salts 4.

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Section: Nucleophilic Addition Of Organometallic Reagents To N-acyl P...mentioning

confidence: 99%

Section: Nucleophilic Addition Of Organometallic Reagents To N-acyl P...mentioning

confidence: 99%

Section: Diastereoselective 14-addition Controlled By Pyridine 3-subs...mentioning

confidence: 99%

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Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition toN-Activated Pyridines

et al. 2012

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Regio- and stereoselective synthesis of 1,4-dihydropyridines by way of an intramolecular interaction of a thiocarbonyl or carbonyl with a pyridinium nucleus

et al. 2001

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Stereoselective synthesis of 1,2- and 1,4-dihydropyridines by using cation–π interaction as a conformation-controlling tool

Yamada

Saitoh

Misono

2002

Tetrahedron Letters

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Stereoselective formation of 4-substituted-1,4-dihydronicotinoyl complexes utilizing the chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]

Cited by 13 publications

References 29 publications

Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition toN-Activated Pyridines

Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition toN-Activated Pyridines

Regio- and stereoselective synthesis of 1,4-dihydropyridines by way of an intramolecular interaction of a thiocarbonyl or carbonyl with a pyridinium nucleus

Stereoselective synthesis of 1,2- and 1,4-dihydropyridines by using cation–π interaction as a conformation-controlling tool

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