<i>aza</i>-Baylis−Hillman Reaction

Declerck, Valérie; Martinez, Jean; Lamaty, Frédéric

doi:10.1021/cr068057c

Cited by 532 publications

(101 citation statements)

References 200 publications

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“…A similar 1,3-difunctionalization (b-amino ketone) is given by the so-called aza-Baylis-Hillman reaction [30]. Retrosynthetic analysis of these compounds suggests the reaction of an imine with the corresponding a,b-unsaturated ester.…”

Section: 2-difunctional Compoundsmentioning

confidence: 92%

Logic of organic chemistry

2016

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A system of logic disconnection or construction of organic molecules is given to overcome serious problems in the study of organic chemistry. Based on the logic system of polar reactions of donors and acceptors several different reactions can be created to access a required target molecule. By a following careful analysis of these proposals several transformations can be detected as the preferred ones. Moreover, by the introduction of the ''umpolung'' principle additional options are given to synthesize a required molecule. These considerations were discussed in the 1,2-, 1,3-, 1,4-, 1,5-and 1,6-difunctional series.

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Section: 2-difunctional Compoundsmentioning

confidence: 92%

Logic of organic chemistry

2016

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“…[1][2][3][4][5] It involves the condensation of a carbon electrophile with the α position of an activated unsaturated compound (Scheme 1). Aldehydes, ketones and suitably protected imines (aza-MBH reaction) 6 are typical electrophilic components, while alkenes, alkynes and allenes substituted with a carbonyl-, carboxyl-, phosphonate-, or sulfonate-type functionality result in a diversity of unsaturated compounds. The reaction is catalyzed by tertiary amines, typically DABCO (rarely, stronger bases) or phosphines, and proceeds in an elegant, atom-economic and operationally simple manner.…”

Section: Introductionmentioning

confidence: 99%

“…8 The predominating preparative utility of the MBH adducts originates from the susceptibility of the allylic / α,β-unsaturated system to nucleophilic substitution and addition. [3][4][5][6][7][8] The mechanism and the position of the displacements strongly depend on the structure of the substrates and the manipulation conditions (Scheme 2). Attack on the primary MBH adducts, allyl alcohols, typically proceeds according to a mechanism of Michaeltype addition of a nucleophile to the electrophilic terminal carbon of an activated unsaturated system (Scheme 2A).…”

Section: Introductionmentioning

confidence: 99%

“…[3][4][5][6][7][8] The potential of the reactivity of MBH adducts towards phosphorus nucleophiles seems not to have been extensively explored as yet and hardly extends beyond a few types of simple P-compounds and MBH adducts. Dialkyl and trialkyl phosphites, which substitute for the electrophilic components according to the Arbuzov reaction mechanism following the general rules outlined in Scheme 2, have been the most documented.…”

Section: Introductionmentioning

confidence: 99%

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P-C bond formation in reactions of Morita-Baylis-Hillman adducts with phosphorus nucleophiles

Talma¹,

Mucha²

2016

Arkivoc

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Morita-Baylis-Hillman adducts (e.g., activated allyl acetates or bromides) are an unprecedented trifunctional synthetic platform for diverse types of nucleophilic displacements, additions and rearrangements. These reactions can proceed in an inter-or intramolecular manner, and with stereoselective induction. Accordingly, they contribute, as the key steps, to numerous synthetic pathways, including the total syntheses of natural products of various classes and to novel strategies leading to medicinally relevant compounds and commercialized drugs. The synthetic feasibility of the Morita-Baylis-Hillman adducts in organophosphorus chemistry has been explored to a relatively low extent. In this review, we summarize the current state of the art on the formation of the C-P bond by means of the title reactions. The scope of the processes, the stereochemistry of the products and their further synthetic relevance to obtain multifunctional compounds, including those that are biologically active, are summarized.

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“…(5) It produces molecules containing a minimum of three proximal functional groups which are of tremendous potential in synthetic and mechanistic organic chemistry. In fact the wide popularity and applicability of this reaction can be easily understood by publications of a number of major [14][15][16][17][18][19][20][21][22] and mini reviews [23][24][25][26][27][28][29][30] and more than 3200 research articles during the past three decades.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Baylis-Hillman reaction: synthesis of heterocyclic molecules

Basavaiah¹,

Reddy²

2015

Arkivoc

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The Baylis-Hillman (BH) [also known as the Morita-Baylis-Hillman (MBH)] reaction is a versatile atom-economic C-C bond forming reaction between the α-position of activated alkenes and electrophiles under the influence of a catalyst and provides interesting classes of densely functionalized molecules. Its intramolecular version is yet another fascinating reaction by itself, producing various carbocylic and heterocyclic compounds of synthetic and medicinal relevance. Applications of the intramolecular Baylis-Hillman reaction in obtaining heterocyclic molecules of different ring sizes and also to the synthesis of various natural products/bioactive compounds containing heterocyclic frameworks are presented in this brief review.

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aza-Baylis−Hillman Reaction

Cited by 532 publications

References 200 publications

Logic of organic chemistry

Logic of organic chemistry

P-C bond formation in reactions of Morita-Baylis-Hillman adducts with phosphorus nucleophiles

Intramolecular Baylis-Hillman reaction: synthesis of heterocyclic molecules

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