Synthesis of (2S,2′S)-bimorpholine N,N′-quaternary salts as chiral phase transfer catalysts

Lippur, Kristin; Kanger, Tõnis; Kriis, Kadri; Kailas, Tiiu; Müürisepp, Aleksander-Mati; Pehk, Tõnis; Lopp, Margus

doi:10.1016/j.tetasy.2007.01.004

Cited by 13 publications

(5 citation statements)

References 35 publications

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“…Other types of quaternary ammonium salts were also developed as chiral phase-transfer catalysts and applied to the asymmetric alkylation of 7 (Scheme 7). Although tartaric acid derived N-spiro derivative 13 [11] afforded the alkylation products with good enantioselectivity, the other catalysts 14, [12] 15, [13] and 16 [14] resulted in low to moderate enantioselectivities.…”

Section: Alkylationmentioning

confidence: 99%

Recent Developments in Asymmetric Phase‐Transfer Reactions

2013

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Phase-transfer catalysis has been recognized as a powerful method for establishing practical protocols for organic synthesis, because it offers several advantages, such as operational simplicity, mild reaction conditions, suitability for large-scale synthesis, and the environmentally benign nature of the reaction system. Since the pioneering studies on highly enantioselective alkylations promoted by chiral phase-transfer catalysts, this research field has served as an attractive area for the pursuit of "green" sustainable chemistry. A wide variety of asymmetric transformations catalyzed by chiral onium salts and crown ethers have been developed for the synthesis of valuable organic compounds in the past several decades, especially in recent years.

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Section: Alkylationmentioning

confidence: 99%

Recent Developments in Asymmetric Phase‐Transfer Reactions

2013

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“…33 However, selectivity was still low in comparison with the impressive results obtained with Shibasaki’s catalysts 32. Kanger et al investigated the tartaric-acid-derived bimorpholinium catalyst 78 for the asymmetric alkylation of 56 ,34 but the yields and enantioselectivities observed with this catalyst system were only modest.…”

Section: Chiral Phase-transfer Catalystsmentioning

confidence: 99%

“…Besides the attempts of Shibasaki’s group to develop tartaric-acid-derived two-centre quaternary ammonium salt PTCs, MacFarland’s33 and Kanger’s34 groups also investigated the synthesis and application of such catalysts. MacFarland et al synthesized and investigated the TaDiAS-related catalysts 76 and 77 (Scheme 20).…”

Section: Chiral Phase-transfer Catalystsmentioning

confidence: 99%

Towards Tartaric‐Acid‐Derived Asymmetric Organocatalysts

2013

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Tartaric acid is one of the most prominent naturally occurring chiral compounds. Whereas its application in the production of chiral ligands for metal-catalysed reactions has been exhaustively investigated, its potential to provide new organocatalysts has been less extensively explored. Nevertheless, some impressive results, such as the use of TADDOLs as chiral H-bonding catalysts or of tartrate-derived asymmetric quaternary ammonium salt catalysts, have been reported over the last decade. The goal of this article is to provide a representative overview of the potential and the limitations of tartaric acid or TADDOLs in the creation of new organocatalysts and to highlight some of the most spectacular applications of these catalysts, as well as to summarize case studies in which other classes of chiral backbones were better suited.

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“…So ergab das von Weinsäure abgeleitete N-Spiroderivat 13 [11] als Katalysator die Alkylierungsprodukte mit guten Enantioselektivitäten, dagegen führten die anderen Katalysatoren 14, [12] 15 [13] und 16 [14] zu niedrigen bis mittleren Enantioselektivitä-ten.…”

Section: K Maruoka Und S Shirakawaunclassified

Neue Entwicklungen bei asymmetrischen Phasentransferreaktionen

2013

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Die Phasentransferkatalyse bildet eine effiziente Grundlage zur Einführung praktischer Methoden in die organische Synthese, denn sie bietet mehrere Vorteile wie einfache Handhabung, milde Reaktionsbedingungen, die Eignung für großtechnische Synthesen und ein umweltfreundliches Reaktionssystem. Seit den wegweisenden Arbeiten zu hoch enantioselektiven Alkylierungen mit chiralen Phasentransferkatalysatoren ist dieses Forschungsgebiet im Hinblick auf eine umweltverträgliche, nachhaltige Chemie von Interesse, und in den vergangenen Jahrzehnten, vor allem in den letzten Jahren, wurden zahlreiche asymmetrische, durch chirale Oniumsalze und Kronenether katalysierte Umwandlungen für die Synthese wertvoller organischer Verbindungen entwickelt.

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Synthesis of (2S,2′S)-bimorpholine N,N′-quaternary salts as chiral phase transfer catalysts

Cited by 13 publications

References 35 publications

Recent Developments in Asymmetric Phase‐Transfer Reactions

Recent Developments in Asymmetric Phase‐Transfer Reactions

Towards Tartaric‐Acid‐Derived Asymmetric Organocatalysts

Neue Entwicklungen bei asymmetrischen Phasentransferreaktionen

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