Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde

Lake, Fredrik; Moberg, Christina

doi:10.1002/1099-0690(200209)2002:18<3179::aid-ejoc3179>3.0.co;2-a

Cited by 36 publications

(31 citation statements)

References 62 publications

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“…Scheme 42. Aziridine [203] and cyclopropane ring-opening, [204] double Michael addition, [205] lactam formation, [206] and reduction of a nitro group by catalytic transfer hydrogenation. [207] Ts = toluenesulfonyl.…”

Section: 9mentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: 9mentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…It was interesting to note that in the present case, using naphthylalkylamines as nucleophiles, no large excess of amine was needed to obtain the mono adduct, contrary to that previously reported in the case of the ring opening of 2-isopropyl-N-(triflouromethylsulfonyl)aziridine with benzylamine. 20 These reactions are extremely slow, but higher yields within shorter times were obtained by employing microwave irradiation. It was found that after 3 h at 150°C in toluene, a 1.1 : 1 ratio of aziridine 1b and amine afforded sulfonamides 2 in 70% yield.…”

Section: Design Synthesis and Characterisation Of Complexesmentioning

confidence: 99%

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

et al. 2013

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The synthesis and characterisation of copper(I) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*) and their use as catalysts in asymmetric cyclopropanation reactions are reported.All ligands and metal complexes were fully characterised, including crystal structures of some species determined by X-ray diffraction on single crystals. This allowed characterising the very different conformations of the macrocycles which could be induced by different substituents or by metal complexation.The strategy adopted for the ligand synthesis is very flexible allowing several structural modifications. A small library of macrocyclic ligands possessing the same donor properties but with either C 1 or C 2 symmetry was synthesized. Cyclopropane products with both aromatic and aliphatic olefins were obtained in good yields and enantiomeric excesses up to 99%.

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“… Aziridin‐203 und Cyclopropan‐Ringöffnung,204 doppelte Michael‐Addition,205 Lactambildung206 und Reduktion einer Nitrogruppe durch katalytische Transferhydrogenierung 207. Ts=Toluolsulfonyl.…”

Section: Literaturüberblickunclassified

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

Kappe

2004

Angewandte Chemie

247

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Die offene Flamme konnte erst gezielt als Heizquelle für Reaktionsgefäße in der Synthesechemie verwendet werden, nachdem Robert Bunsen 1855 den nach ihm benannten Brenner erfunden hatte. Der Bunsen‐Brenner wurde später durch den Heizpilz, das Ölbad und die Heizplatte als Wärmequellen für chemische Reaktionen abgelöst. In den vergangenen Jahren ist das Erhitzen und Beschleunigen chemischer Reaktionen durch Mikrowellenenergie populär geworden. Diese Heiztechnik hat sich von einer Laborkuriosität zu einer etablierten Methode entwickelt, die an Universitäten und in der Industrie stark genutzt wird. Die effiziente Verringerung der Reaktionszeiten (von Tagen und Stunden auf Minuten und Sekunden) ist nur einer der vielen Vorteile des schnellen Erhitzens mit Mikrowellen (“microwave flash heating”). Dieser Aufsatz gibt einen Überblick über neuere Anwendungen des kontrollierten Mikrowellenerhitzens in der modernen organischen Synthese und diskutiert einige grundlegende Vorgänge.

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Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde

Cited by 36 publications

References 62 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

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