Enamines: recent advances in synthetic, spectroscopic, mechanistic, and stereochemical aspects—II

Hickmott, P. W.

doi:10.1016/0040-4020(82)85027-8

Cited by 162 publications

(46 citation statements)

References 404 publications

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“…The superiority of six-membered, secondary amines over pyrrolidine suggests that nucleophilicity of the nitrogen could play ar ole,a st he highest yieldsw ere obtained for aminesw ith extra heteroatoms (oxygen or nitrogen). [35] These heteroatoms through an inductive effect, withdrawe lectron density from the nitrogen, makingi tl ess nucleophilic. Primary amines failed in catalyzing our modelreaction (entry 9).…”

Section: Models Tudiesmentioning

confidence: 99%

Photocatalytic Reaction of Diazo Compounds with Aldehydes

2016

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Section: Models Tudiesmentioning

confidence: 99%

Photocatalytic Reaction of Diazo Compounds with Aldehydes

2016

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“…Yet, the conclusiveness of the UV/ visible spectroscopic detection method is not unambiguous, because heterocyclic enamines such as 2,3-DP also can undergo condensation with o-aminobenzaldehyde (Cervinka, 1988). Moreover, evidence has been provided that heterocyclic imines such as D 1 -piperideine, which builds the core structural element of 1,2-DP, can indeed react as their heterocyclic enamine tautomers in the o-aminobenzaldehyde reaction (Harada et al, 1970;Hickmott, 1982). Together, these findings strongly argue against the possibility to discriminate between 1,2-DP and 2,3-DP by the o-aminobenzaldehyde reaction and subsequent UV/visible spectroscopic analysis.…”

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confidence: 99%

Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity

et al. 2017

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The nonprotein amino acid pipecolic acid (Pip) regulates plant systemic acquired resistance and basal immunity to bacterial pathogen infection. In Arabidopsis (Arabidopsis thaliana), the lysine (Lys) aminotransferase AGD2-LIKE DEFENSE RESPONSE PROTEIN1 (ALD1) mediates the pathogen-induced accumulation of Pip in inoculated and distal leaf tissue. Here, we show that ALD1 transfers the a-amino group of L-Lys to acceptor oxoacids. Combined mass spectrometric and infrared spectroscopic analyses of in vitro assays and plant extracts indicate that the final product of the ALD1-catalyzed reaction is enaminic 2,3-dehydropipecolic acid (DP), whose formation involves consecutive transamination, cyclization, and isomerization steps. Besides L-Lys, recombinant ALD1 transaminates L-methionine, L-leucine, diaminopimelate, and several other amino acids to generate oxoacids or derived products in vitro. However, detailed in planta analyses suggest that the biosynthesis of 2,3-DP from L-Lys is the major in vivo function of ALD1. Since ald1 mutant plants are able to convert exogenous 2,3-DP into Pip, their Pip deficiency relies on the inability to form the 2,3-DP intermediate. The Arabidopsis reductase ornithine cyclodeaminase/m-crystallin, alias SYSTEMIC ACQUIRED RESISTANCE-DEFICIENT4 (SARD4), converts ALD1-generated 2,3-DP into Pip in vitro. SARD4 significantly contributes to the production of Pip in pathogen-inoculated leaves but is not the exclusive reducing enzyme involved in Pip biosynthesis. Functional SARD4 is required for proper basal immunity to the bacterial pathogen Pseudomonas syringae. Although SARD4 knockout plants show greatly reduced accumulation of Pip in leaves distal to P. syringae inoculation, they display a considerable systemic acquired resistance response. This suggests a triggering function of locally accumulating Pip for systemic resistance induction.

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“…Enamines, which are neutral nucleophiles, have been used in a number of reactions, 5,6 although they can be quite unstable under hydrolytic or oxidative conditions. On the other hand, the amide group is a stable functional group and amides can be easily isolated.…”

Section: Scheme 1 Overview Of Enaminonesmentioning

confidence: 99%

2,3-Dihydropyridin-4(1H)-ones and 3-Aminocyclohex-2-enones: Synthesis, Functionalization, and Applications to Alkaloid Synthesis

Seki¹,

Georg²

2014

Synlett

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This account summarizes our recent investigations into the chemistry of 2,3-dihydropyridin-4(1H)-ones and 3-aminocyclohex-2-enones (enaminones). These enaminones are exceptionally versatile chemical scaffolds that serve as valuable intermediates in the synthesis of indolizidine and quinolizidine alkaloids and other bioactive compounds. Since we reported our first method for constructing enaminones in 2006, we have developed a number of additional approaches to the synthesis and derivatization of enaminones and we have explored their applications in natural product synthesis.

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Enamines: recent advances in synthetic, spectroscopic, mechanistic, and stereochemical aspects—II

Cited by 162 publications

References 404 publications

Photocatalytic Reaction of Diazo Compounds with Aldehydes

Photocatalytic Reaction of Diazo Compounds with Aldehydes

Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity

2,3-Dihydropyridin-4(1H)-ones and 3-Aminocyclohex-2-enones: Synthesis, Functionalization, and Applications to Alkaloid Synthesis

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