Platinum(II) Chloride-Catalyzed Stereoselective Domino Enyne Isomerization/Diels−Alder Reaction

Schelwies, Mathias; Farwick, Andreas; Röminger, Frank; Helmchen, Günter

doi:10.1021/jo1014068

Cited by 20 publications

(4 citation statements)

References 15 publications

(14 reference statements)

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“…64 The use of 1,6-enynes deriving from Ir-catalysed AAS has also been reported by Helmchen et al who exploited a Pt-catalysed domino enyne isomerisation/Diels-Alder sequence for the synthesis of complex heterocycles. 65 An elegant strategy for the systematic synthesis of 2,5-disubstituted pyrrolidines has been developed by Helmchen and coworkers. This methodologies relies on the Ir-catalysed asymmetric allylic amination of carbonates with N,N-diacylamines and the subsequent conversion of the resulting alkene functionality into an alkylborane to be used for Suzuki-Miyaura couplings with iodoacrylate 70.…”

Section: Nitrogen Nucleophilesmentioning

confidence: 99%

Recent advances and applications of iridium-catalysed asymmetric allylic substitution

2012

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Since their discovery in 1997, iridium-catalysed asymmetric allylic substitutions have been developed into a broadly applicable tool for the synthesis of chiral building blocks via C-C and C-heteroatom bond formation. The remarkable generality of these reactions and the high levels of regio- and enantioselectivity that are usually obtained in favour of the branched products have been made possible by a thorough investigation of the catalyst system and its mode of action. Therefore, today the Ir-catalysed asymmetric allylic substitution is a powerful reaction in the organic chemist's repertoire and has been used extensively for several applications. This article aims to provide an overview of the development of iridium catalysts derived from an Ir salt and a chiral phosphoramidite and their application to the enantioselective synthesis of natural products and biologically relevant compounds.

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Section: Nitrogen Nucleophilesmentioning

confidence: 99%

Recent advances and applications of iridium-catalysed asymmetric allylic substitution

2012

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“…118 As shown in Scheme 1.77, heating a mixture of these 1,6-enynes and various dienophiles in the presence of PtCl 2 in toluene led to the corresponding domino bi-or tricyclic cycloadducts in moderate to good yields as single diastereomers in all cases of the substrates studied. A novel route towards chiral aminocyclopentanols was reported by Gre´e et al, in 2011.…”

Section: Miscellaneous Domino Reactionsmentioning

confidence: 97%

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

2013

Asymmetric Domino Reactions

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This chapter updates the recent developments in asymmetric one-, two-, and multicomponent domino reactions which involve chiral substrates. It is divided into two sections, dealing successively with one- and two-component domino reactions, and with multicomponent domino reactions. The first section is subdivided into eight sections, describing domino reactions with an anionic primary step, domino reactions based on cationic sequences, domino reactions initiated by a pericyclic primary step, domino reactions based on carbene sequences, palladium-catalysed domino reactions, ruthenium-catalysed domino reactions, gold-catalysed domino reactions, and finally miscellaneous domino reactions. The second section of the chapter is subdivided into 10 sections, dealing with multicomponent reactions initiated by the Michael addition, multicomponent reactions based on the Hantzsch reaction, multicomponent reactions based on the Ugi reaction, multicomponent reactions based on the Strecker reaction, multicomponent reactions based on the Mannich reaction, multicomponent reactions initiated by an allylation reaction, multicomponent reactions based on the Passerini reaction, multicomponent reactions based on the Biginelli reaction, multicomponent reactions based on the Petasis reaction, and finally miscellaneous multicomponent reactions. The power and utility of these reactions are well illustrated by their application in the synthesis of a wide range of structurally diverse and complex chiral molecules.

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“…In 2010, Helmchen and co-workers reported a novel route to highly enantioenriched complex heterocycles on the basis of asymmetric domino platinum-catalyzed enyne isomerization/Diels–Alder cycloaddition reaction of enantiopure 1,6-enynes . As shown in Scheme , heating a mixture of these 1,6-enynes 273a , b and various dienophiles 274a – d in the presence of PtCl 2 in toluene led to the corresponding domino bi- or tricyclic cycloadducts 275a – e in moderate to good yields as single diastereomers in all cases of substrates studied.…”

Section: One- and Two–component Domino Reactionsmentioning

confidence: 99%

Stereocontrolled Domino Reactions

2012

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AS 2.8.4. Other Domino Reactions AT 3. Multicomponent Reactions AU 3.1. Multicomponent Reactions Initiated by the Michael Reaction AU 3.1.1. Multicomponent Reactions Initiated by a Classical Michael Reaction AU 3.1.2. Multicomponent Reactions Initiated by a Hetero-Michael Reaction AW 3.2. Multicomponent Hantzsch Reactions AZ 3.3. Multicomponent Ugi Reactions AZ 3.4. Multicomponent Strecker Reactions BG 3.5. Multicomponent Mannich Reactions BH 3.6. Multicomponent Reactions Initiated by an Allylation Reaction BI 3.7. Multicomponent Passerini Reactions BK 3.8. Multicomponent Biginelli Reactions BM 3.9. Multicomponent Petasis Reactions BN 3.10. Miscellaneous Multicomponent Reactions BP 3.10.1. Metal-Catalyzed Multicomponent Reactions BP 3.10.2. Other Multicomponent Reactions BT 4. Conclusion BZ Author Information BZ Biography CA Abbreviations CA References CA

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Platinum(II) Chloride-Catalyzed Stereoselective Domino Enyne Isomerization/Diels−Alder Reaction

Cited by 20 publications

References 15 publications

Recent advances and applications of iridium-catalysed asymmetric allylic substitution

Recent advances and applications of iridium-catalysed asymmetric allylic substitution

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

Stereocontrolled Domino Reactions

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