One-Pot Synthesis of Optically Active β-Amino-α-methylene Carbonyl Derivatives From α-Amidosulfones Using Quinine-Based Phase-Transfer Catalysts

Mazzotta, Stefano; Gramigna, Lucia; Bernardi, Luca; Ricci, Alfredo

doi:10.1021/op1000308

Cited by 22 publications

(5 citation statements)

References 20 publications

(25 reference statements)

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“…[125] Optically active b-amino-a-methylene derivatives (aza-Morita-Baylis-Hillman adducts), such as 158, were prepared by using a one-pot protocol involving the enantioselective Mannich reaction of 157 catalyzed by 2 n, followed by a Horner olefination (Scheme 97). [126] Jørgensen and co-workers reported an asymmetric monofluorovinylation through an enantioselective Mannich reaction of a-fluoro-b-keto-benzothiazolesulfone, such as 159, with in situ generated N-benzyloxycarbonylimine (N-Cbz-imine) in the presence of catalyst 2 o. Reduction of the Mannich product with LiBH 4 gave (E)-160 with good enantioselectivity (Scheme 98).…”

Section: à C Bond Formationmentioning

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: à C Bond Formationmentioning

confidence: 99%

Recent Developments in Asymmetric Phase‐Transfer Reactions

2013

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“…Aza-Morita-Baylis-Hillman adducts were also obtained via a one-pot Horner-type olefination in combination with a Mannich reaction (Scheme 32). 63 In this context, Bernardi, Ricci and co-workers demonstrated that good yields and excellent enantioselectivities were observed through this process in the presence of phase-transfer catalyst 10a. O O R 3 O R 3 O R 1 = M e , O R R 2 = a l k y l R 3 = pt o l y l , 2 -t r i m e t h y l s i l y l e t h y Alternatively to Mannich reactions, the [4+2] cycloadditions of ketenes and imines can be used in the construction of Mannich-type adducts, such as b-amino carbonyl compounds.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Recent Applications of α-Amido Sulfones as in situ Equivalents of Activated Imines for Asymmetric Catalytic Nucleophilic Addition Reactions

Yin¹,

Zhang²,

Xu³

2010

Synthesis

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Catalytic nucleophilic addition to the carbon-nitrogen double bond of an imino group in an asymmetric fashion provides a direct connective and attractive route to enantioenriched N-protected amines with structural diversity. In the last decades, significant achievements have been made in the field of catalytic enantioselective reactions involving the use of a-amido sulfones as in situ equivalents of activated imines. These, in combination with diverse nucleophiles, are used to prepare optically pure amines or N-protected amides. This review focuses on the recent advances in the synthetic applications of a-amido sulfones as reactive precursors of imines in the asymmetric addition of organometallic reagents, Mannich, aza-Henry, Strecker, and other asymmetric nucleophilic addition reactions.

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“…158, wurden in einer Eintopfreaktion durch enantioselektive Mannich-Reaktion von 157 in Gegenwart des Katalysators 2 n und nachfolgende Horner-Olefinierung hergestellt (Schema 97). [126] Jørgensen et al berichteten über eine asymmetrische Monofluorvinylierung durch enantioselektive Mannich-Reaktion des a-Fluor-b-ketobenzothiazolsulfons 159 mit in situ hergestelltem N-Benzyloxycarbonyl(N-Cbz)-Imin in Gegenwart des Katalysators 2 o. Die Reduktion des Mannich-Produkts mit LiBH 4 führte mit guter Enantioselektivität zu E-160 (Schema 98).…”

Section: Phasentransferreaktionenunclassified

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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One-Pot Synthesis of Optically Active β-Amino-α-methylene Carbonyl Derivatives From α-Amidosulfones Using Quinine-Based Phase-Transfer Catalysts

Abstract: Optically active β-amino-α-methylene carbonyl derivatives (aza-Morita−Baylis−Hillman adducts) were prepared using a one-pot protocol involving an enantioselective Mannich reaction catalyzed by various quinine-based catalysts, followed by a Horner olefination.

Cited by 22 publications

References 20 publications

Recent Developments in Asymmetric Phase‐Transfer Reactions

Recent Developments in Asymmetric Phase‐Transfer Reactions

Recent Applications of α-Amido Sulfones as in situ Equivalents of Activated Imines for Asymmetric Catalytic Nucleophilic Addition Reactions

Neue Entwicklungen bei asymmetrischen Phasentransferreaktionen

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