Catalytic Enantioselective Addition of Organometallic Reagents to <i>N</i>-Formylimines Using Monodentate Phosphoramidite Ligands

Pizzuti, Maria Gabriella; Minnaard, Adriaan J.; Feringa, Ben L.

doi:10.1021/jo702140f

Cited by 62 publications

(19 citation statements)

References 43 publications

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“…Zu diesen gehören Dialkylzink-und Trialkylaluminiumreagentien, wobei die Zinkderivate höhere Enantioselektivitäten liefern. [188] Die Imine 86 entstehen in situ aus den a-Amidosulfonen 85 durch Deprotonierung mit einem zusätzlichen ¾quivalent Dialkylzink (Schema 25). Mit dem Phosphor- [189] Die konjugierte Addition von Diethylzinkreagentien an a-Halogen-substituierte Cyclohexenone 89 wurde ebenfalls beschrieben.…”

Section: Abfangen Von Reaktionszwischenstufen Mit Elektrophilenunclassified

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

2010

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Die asymmetrische Katalyse mit Übergangsmetallkomplexen ist die Grundlage unzähliger stereoselektiver Umwandlungen und hat damit das Bild der modernen Synthesechemie gewandelt. Der Schlüssel zum Erfolg war die Entwicklung chiraler Liganden zur Kontrolle der Regio‐, Diastereo‐ und Enantioselektivität. Dabei haben sich Phosphoramidite als eine äußerst vielseitige und leicht zugängliche Klasse von chiralen Liganden erwiesen. Ihre modulare Struktur ermöglicht die Herstellung von Ligandenbibliotheken und erleichtert die Feinabstimmung für eine bestimmte katalytische Reaktion. Phosphoramidite bewirken oft außerordentlich hohe Stereoselektivitäten, und ihre einzähnige Natur ist in der kombinatorischen Katalyse, die gemischte Liganden verwendet, unverzichtbar. In diesem Aufsatz werden neue Entwicklungen in der asymmetrischen Katalyse mit Phosphoramiditen diskutiert, wobei der Schwerpunkt auf der Bildung von Kohlenstoff‐ Kohlenstoff‐ und Kohlenstoff‐Heteroatom‐Bindungen liegt.

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Section: Abfangen Von Reaktionszwischenstufen Mit Elektrophilenunclassified

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

2010

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“…Additives are also commonly used for these reactions. Therefore, in order to see the effect of additives on our catalyst system i Pr 2 NEt, Et 3 N, HMPA, DABCO, MeOH, and TMEDA were tried (entries [15][16][17][18][19][20]. After observing that TMEDA increased the enantioselectivity, it was decided to do further optimization by changing the amount and also the type of copper salt.…”

Section: Resultsmentioning

confidence: 99%

“…polymer-supported L-prolinol catalyst. 15 Besides N -sulfonyl and N -phosphinoyl imines, this reaction was also studied with BOC and formyl protected imines by Aleksakis et al 16 and Feringa et al 17 respectively.…”

Section: Introductionmentioning

confidence: 99%

PFAM catalyzed enantioselective diethylzinc addition to imines

Doğan¹,

Çağli²

2015

Turk J Chem

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Chiral amines are important starting materials for the synthesis of biologically important compounds.Enantioselective addition of dialkylzinc reagents to imines is a reliable method for the synthesis of these compounds.Different chiral catalysts were developed and used for this method. Phosphorous based PFAM catalysts were tried for the first time in the enantioselective synthesis of amines by reacting diethylzinc with N-sulfonyl imines and Ndiphenylphosphinoyl imines. Chiral amines were isolated with moderate to acceptable yields and enantioselectivities.

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“…Aromatic aldehydes reacted smoothly to give the corresponding b-amino ketone derivatives 27 in high yield (Table 12, entries [7][8][9][10][11][12][13][14]. The reaction worked well with a variety of aldehydes including those bearing an electron withdrawing group, and the corresponding b-amino ketones 27 were obtained with very good yields.…”

Section: Bismuth-mediated Three-component Mannich-type Reactionmentioning

confidence: 94%

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

Ollevier

2011

Bismuth-Mediated Organic Reactions

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Bismuth triflate was found to be an efficient catalyst both in the Mannich-type reaction of silyl enolates and in the Sakurai reaction of allyltrimethylsilane with N-alkoxycarbonylamino sulfones. The reactions proceeded smoothly with a low catalyst loading of Bi(OTf)(3)·4H(2)O (0.5-5.0 mol%) to afford the corresponding protected β-amino carbonyl compounds and homoallylic amines in very good yields (up to 96%). The latter compounds could also be obtained via a bismuth-mediated three-component reaction. We have also developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in a low catalyst loading (1 mol%). The reaction proceeds rapidly and affords the corresponding 5-[hydroxy(aryl)methyl]furan-2(5H)-ones in high yields with good to very good diastereoselectivities (diastereoisomeric ratios>98:2). Such selectivities, although previously reported with other Lewis acids, could be achieved with a much lower catalyst loading. 5-[Hydroxy(alkyl)methyl]furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities. The vinylogous Mukaiyama aldol reaction has also been extended to 2,2-dimethyl-6-methylene-4-(trimethyl-silyloxy)-1,3-diox-4-ene using 1 mol% of Bi(OTf)(3)·4H(2)O.

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Catalytic Enantioselective Addition of Organometallic Reagents to N-Formylimines Using Monodentate Phosphoramidite Ligands

Cited by 62 publications

References 43 publications

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

PFAM catalyzed enantioselective diethylzinc addition to imines

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

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