Hetero Diels-Alder reactions in organic chemistry

Tietze, Lutz F.; Kettschau, Georg

doi:10.1007/bfb0119240

Cited by 382 publications

(145 citation statements)

References 550 publications

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“…The general, most universal method of the preparation of six-membered cyclic nitronates is a hetero Diels-Alder (HDA) reaction between conjugated nitroalkenes (CNA) as heterodienes and ethylenic dienophiles [3][4][5][6]. Most of these reactions follow the one-step [4 ?…”

Section: Introductionmentioning

confidence: 99%

An experimental and theoretical study of the hetero Diels–Alder reactions between (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether: one-step or zwitterionic, two-step mechanism?

Jasiński

Kubik

Łapczuk-Krygier

et al. 2014

Reac Kinet Mech Cat

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The mechanistic aspects of the hetero Diels-Alder reactions between strongly electrophilic (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether have been analyzed on the basis of kinetic experimental results as well as quantum chemical simulations of reaction paths. These reactions may theoretically proceed via one step or stepwise, zwitterionic mechanism. It was found that the conversion of addends into adducts carried out via polar, but not zwitterionic mechanism. This is confirmed by kinetic substituent and solvent effects. Subsequently, a detailed analysis of internal reaction coordinate trajectories shows that the title reactions should be considered as examples of ''two-stage one-step'' cycloadditions according to Domingo terminology.

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Section: Introductionmentioning

confidence: 99%

An experimental and theoretical study of the hetero Diels–Alder reactions between (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether: one-step or zwitterionic, two-step mechanism?

Jasiński

Kubik

Łapczuk-Krygier

et al. 2014

Reac Kinet Mech Cat

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“…18 The most common HDA cycloadditions have been directed towards the synthesis of pyran derivatives as carbohydrate precursors; in this, we have extended the use of our enantio-pure sulfinyl homoand hetero-dienes.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Diels-Alder reactivity of sulfinyl homo- and heterodienes obtained via enantiopure sulfenic acids

Aversa¹,

Barattucci²,

Bonaccorsi³

et al. 2002

Arkivoc

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This account is intended to provide a brief survey on our contribution in the field of enantiopure sulfinyl homo and hetero dienes which we are able to obtain via enantiopure sulfenic acids. The chemistry of these sulfinyl-dienes was mainly developed taking into account the practical importance of stereoselective homo and hetero Diels-Alder cycloadditions, able to supply useful intermediates in the synthesis of target molecules.

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“…33,34 Among various synthetic methodologies available, asymmetric hetero-Diels-Alder has emerged as one of the most powerful tools for the construction of complex six-membered heterocyclic systems found in the plethora of natural products and active pharmaceutical ingredients. 35,36 As was the case for DA reactions, rare-earth metal(III) triflates have also been successfully employed to promote heteroDiels-Alder reactions. [10][11][12][13][14][15] Below are notable examples of M(OTf) 3 -catalyzed HDA reactions published in the last five years.…”

Section: Hetero-diels-alder Reactionsmentioning

confidence: 99%

Recent applications of rare-earth metal(III) triflates in cycloaddition and cyclization reactions

Ladziata¹

2014

Arkivoc

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Rare-earth metal(III) triflates are extremely mild, efficient and water-tolerable Lewis acid catalysts for a wide range of organic transformations. Rare-earth metal triflates retain activity even in the presence of multiple Lewis bases containing oxygen, nitrogen, sulfur and phosphorus atoms, and can be easily recovered and reused without any loss of catalytic activity. This review summarizes recent developments and highlights key applications of these unique Lewis acids in cycloaddition and cyclization reactions.

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Hetero Diels-Alder reactions in organic chemistry

Cited by 382 publications

References 550 publications

An experimental and theoretical study of the hetero Diels–Alder reactions between (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether: one-step or zwitterionic, two-step mechanism?

An experimental and theoretical study of the hetero Diels–Alder reactions between (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether: one-step or zwitterionic, two-step mechanism?

Synthesis and Diels-Alder reactivity of sulfinyl homo- and heterodienes obtained via enantiopure sulfenic acids

Recent applications of rare-earth metal(III) triflates in cycloaddition and cyclization reactions

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