A Practical Synthesis of (<i>S</i>)-2-Cyclohexyl-2-phenylglycolic Acid via Organocatalytic Asymmetric Construction of a Tetrasubstituted Carbon Center

Tokuda, Osamu; Kano, Taichi; Gao, Weiguo; Ikemoto, Tokutaka; Maruoka, Keiji

doi:10.1021/ol052164w

Cited by 112 publications

(31 citation statements)

References 21 publications

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“…The use of different unsymmetrical ketones as acceptors in proline-catalyzed aldolizations was later accomplished, which allowed the concise synthesis of compounds with a quaternary carbon center. [46] An impressive advance in the area of aldol chemistry was reported by Northrup and MacMillan, who documented the first direct enantioselective catalytic cross-aldol reaction of two unmodified aldehydes: a powerful transformation (Scheme 12). [47] This reaction requires that the non-equivalent aldehydes selectively partition into two discrete components-the nucleophilic donor and the electrophilic acceptor.…”

Section: Proline-catalyzed Nucleophilic Additionsmentioning

confidence: 99%

“…[13c] The use of TEMPO (46), a persistent radical reagent, to intercept the radical cationic species affords the desired oxygenated adducts 47 in moderate to high enantioselectivity. Although the same products are accessible by the highly stereoselective proline-catalyzed addition of aldehydes to nitrosobenzene and molecular oxygen (Section 3.4.3), this study represented a significant proof of concept for SOMO catalysis.…”

Section: Radical Aminocatalysismentioning

confidence: 99%

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Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry

Marigo²,

et al. 2008

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Catalysis with chiral secondary amines (asymmetric aminocatalysis) has become a well-established and powerful synthetic tool for the chemo- and enantioselective functionalization of carbonyl compounds. In the last eight years alone, this field has grown at such an extraordinary pace that it is now recognized as an independent area of synthetic chemistry, where the goal is the preparation of any chiral molecule in an efficient, rapid, and stereoselective manner. This has been made possible by the impressive level of scientific competition and high quality research generated in this area. This Review describes this "Asymmetric Aminocatalysis Gold Rush" and charts the milestones in its development. As in all areas of science, progress depends on human effort.

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Section: Proline-catalyzed Nucleophilic Additionsmentioning

confidence: 99%

Section: Radical Aminocatalysismentioning

confidence: 99%

Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry

Marigo²,

et al. 2008

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“…l-Proline has been found to be effective for the direct aldol reaction of a-keto esters with a limited number of aldehydes and cyclohexanone [28,29].…”

Section: Asymmetric Aldol Reactionsmentioning

confidence: 99%

Asymmetric Organocatalysis

Liu

Gong

2011

Asymmetric Catalysis From a Chinese Perspective

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Asymmetric organocatalysis has been receiving considerable attention in the last decade and thereby made tremendous advances. Chinese researchers have also intensified efforts to investigate asymmetric organocatalysis by using diverse types of disciplines, including enamine, iminium, Brønsted acid, carbene, and Lewis base catalysis. As a result, a large number of excellent catalysts and elegant protocols have come out from China. This article summarizes the most representative achievements in enantioselective organocatalysis from Chinese groups.

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“…Später gelangen auch prolinkatalysierte Aldolisierungen mit unsymmetrischen Ketonen, die Produkte mit einem quartären Kohlenstoffzentrum ergaben. [46] MacMillan und Mitarbeitern entwickelten eine direkte enantioselektive katalytische gekreuzte Aldolreaktion zweier nichtmodifizierter Aldehyde (Schema 12). [47] Bei dieser Umsetzung muss jeweils einer der beiden Aldehyde als nucleophiler Donor und elektrophiler Akzeptor auftreten.…”

Section: Aldehyde Als Donorenunclassified

Die asymmetrische Aminokatalyse – Goldrausch in der organischen Chemie

Marigo²,

et al. 2008

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Die Katalyse mit chiralen sekundären Aminen (asymmetrische Aminokatalyse) ist ein leistungsfähiges Verfahren zur chemo‐ und enantioselektiven Funktionalisierung von Carbonylverbindungen. Allein in den letzten acht Jahren wuchs dieses Feld zu einem eigenständigen Teilgebiet der Synthesechemie heran, dessen Ziel es sein muss, jede beliebige chirale Verbindung effizient, rasch und stereoselektiv herzustellen. Möglich wurde dieser Fortschritt durch hochqualifizierte Forschung und einen eindrucksvollen wissenschaftlichen Wettbewerb. Dieser Aufsatz beschreibt den “Goldrausch der asymmetrischen Aminokatalyse” und weist auf die Meilensteine dieser Entwicklung hin. Wie auf allen Wissenschaftsgebieten gilt letztlich: Der Fortschritt hängt vom Menschen ab.

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A Practical Synthesis of (S)-2-Cyclohexyl-2-phenylglycolic Acid via Organocatalytic Asymmetric Construction of a Tetrasubstituted Carbon Center

Cited by 112 publications

References 21 publications

Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry

Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry

Asymmetric Organocatalysis

Die asymmetrische Aminokatalyse – Goldrausch in der organischen Chemie

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