Corrigendum to “A parallel combinatorial approach to locating homochiral Lewis acid catalysts for the asymmetric aza-Diels–Alder reaction of an imino dienophile”

Bundu, Abas; Guillarme, Stéphane; Hannan, John J.; Wan, Hayley; Whiting, Andrew

doi:10.1016/j.tetlet.2003.08.084

Cited by 8 publications

(2 citation statements)

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“…This led the authors to suggest the presence of temperature-dependent multiple catalyst species (dimeric or oligomeric) or the existence of an achiral background reaction that persists at lower temperatures. Use of other metals such as MgI 2 or FeCl 3 afforded the adduct in >90% yields; however, it should be noted that the reproducibility of these results has been questioned …”

Section: Cycloaddition Reactions Of Imines and Hydrazonesmentioning

confidence: 99%

Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update

et al. 2011

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Section: Cycloaddition Reactions Of Imines and Hydrazonesmentioning

confidence: 99%

Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update

et al. 2011

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“…The use of ytterbium(III) triflate 56 was shown by Whiting et al to catalyse the aza-Diels-Alder reaction asymmetrically. 57 However, as with many aza-Diels-Alder examples, these reactions proved difficult to reproduce and scale up, 58 which prompted the development of robust catalytic asymmetric methods. Prior to this, it was necessary to clearly understand the reaction mechanism as it was generally accepted that the aza-Diels-Alder reaction This journal is © The Royal Society of Chemistry 2011 could either proceed through a concerted (either standard or inverse electron-demand Diels-Alder cycloadditions) or a stepwise process.…”

Section: Methodsmentioning

confidence: 99%

Mannich–Michael versus formal aza-Diels–Alder approaches to piperidine derivatives

2011

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A review into the aza-Diels-Alder reaction, mainly concentrating on literature examples that form piperidin-4-ones from the reaction of imines and electron rich dienes or enones, either through a Lewis acidic/Brønsted acid approach or through the use of an organocatalyst. This review questions whether the mechanism of the aza-Diels-Alder reaction is step wise as opposed to concerted when using oxygenated dienes.

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Diels‐Alder Reactions of Imino Dienophiles

et al. 2005

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In comparison to all carbon [4 + 2] cycloadditions, Diesl‐Alder reactions are still in their infancy. The last four decades, however, have seen intensive research in this area. The results if that synthetic organic chemists now have a powerful tool at their disposal for rapid construction of highly functionalized six‐membered nitrogen heterocycles, often in a regio‐, diastereo‐, and enantioselective manner. This chapter encompasses the topic of imine[4 + 2] cycloaddition reactions, of which there are a number of variants. This chapter is limited exclusively to imine and iminium ion dienophiles that undergo inter‐ and intramolecular Diels‐Alder reactions with acylic and cyclic all‐carbon 1,3‐dienes affording 1,2,5,6‐tetrahydropyridines as the initial cycloadducts. In situations where there is a mechanistic ambiguity, such as reactions that proceed via Mannich reactions, these mechanisms are included since it is difficult to know where to draw the line on coverage. A comprehensive discussion of each structural type of imino dienophiles covers the literature up to the middle of 2004. A general overview of mechanistic, regiochemical, and sterochemical considerations is also presented. Specific relevant exo/endo issues, remote diasteroselectivity and the use of chiral auxiliaries are discussed under each separate imine type. Separate sections have also been included that describe intramolecular reactions, as well as more recent advances in enantioselective cycloadditions involving chiral catalysts.

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Corrigendum to “A parallel combinatorial approach to locating homochiral Lewis acid catalysts for the asymmetric aza-Diels–Alder reaction of an imino dienophile”

Cited by 8 publications

References 2 publications

Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update

Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update

Mannich–Michael versus formal aza-Diels–Alder approaches to piperidine derivatives

Diels‐Alder Reactions of Imino Dienophiles

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