The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids

Feng, Jingchao; Yan, Wenjin; Wang, Dong; Li, Peng; Sun, Quantao; Wang, Rui

doi:10.1039/c2cc33200k

Cited by 183 publications

(47 citation statements)

References 66 publications

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“…The only reports of asymmetric alkylation of indole are at C3 position. 8 There are only two reports of the alkylation of the indole nitrogen to form the acyclic aminal, but none asymmetrically. 9 Antilla et.…”

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confidence: 99%

Controlling Regioselectivity in the Enantioselective N‐Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc‐ProPhenol

2017

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The enantioselective N-alkylation of indole and its derivatives with aldimines is efficiently catalyzed by a zinc-ProPhenol dinuclear complex under mild conditions to afford N-alkylated indole derivatives in good yield (up to 86%) and excellent enantiomeric ratio (up to 99.5: 0.5 e.r.). This protocol tolerates a wide array of indoles, as well as pyrrole and carbazole, to afford the corresponding N-alkylation products. The reaction can be run on gram scale with reduced catalyst loading without impacting the efficiency. The chiral aminals were further elaborated into various chiral polyheterocyclic derivatives. The surprising stability of the chiral N-alkylation products will open new windows for asymmetric catalysis and medicinal chemistry.

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confidence: 99%

Controlling Regioselectivity in the Enantioselective N‐Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc‐ProPhenol

2017

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“…7 Very recently, Wang and co-workers reported the asymmetric addition of 1,3-dicarbonyl compounds onto N -alkoxycarbonyl ketimines and asymmetric aza -Friedel-Craft reaction of indoles and pyrroles with N -Boc ketimines in the presence of chiral phosphoric acid catalysts; 8 the latter led to the formation of 3-aminooxindoles in good yields with excellent enantioselectivities. 9 …”

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confidence: 99%

Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Wei

Shi

et al. 2013

Org. Biomol. Chem.

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Asymmetric catalytic aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with MVK has been established by using chiral amino and phosphino catalysts. The reaction resulted in biomedically important 3-substituted 3-amino-2-oxindoles in good yields (>80% for most cases) and excellent enantioselectivity (90–99%ee). Twenty-eight cases assembled with chiral quaternary stereogenic centers have been examined under convenient systems.

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“…Indoles are, in general, suitablen ucleophilesf or the Friedel-Craftsa lkylation reactionb ym eanso fc hiral phosphoric acid, whereasp yrroles have not been extensively employed due to their low nucleophilicity. [16][17] Interestingly,p yrroles gave better results than indoles in the present reaction.…”

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confidence: 60%

Enantioselective Friedel–Crafts Alkylation Reaction of Heteroarenes with N‐Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid

Miyagawa

Yoshida

Kiyota

et al. 2019

Chemistry A European J

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An enantioselective Friedel–Crafts alkylation reaction of pyrroles and indoles with N‐unprotected trifluoromethyl ketimines by use of chiral phosphoric acid provided α‐trifluoromethylated primary amines bearing chiral tetrasubstituted carbon centers in high yields and with high to excellent enantioselectivities. The present reaction is unique to N‐unprotected trifluoromethyl ketimines. No reaction took place with N‐p‐methoxyphenyl (PMP)‐substituted ketimine. Corresponding α‐trifluoromethylated amines were transformed without loss of enantioselectivity.

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The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids

Abstract: The first asymmetric aza-Friedel-Crafts reaction of indoles and pyrroles with isatin-derived N-Boc ketimines catalyzed by chiral phosphoric acids is reported. In general, derivatives of substituted 3-amino-2-oxindoles were obtained with excellent enantioselectivities and high yields.

Cited by 183 publications

References 66 publications

Controlling Regioselectivity in the Enantioselective N‐Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc‐ProPhenol

Controlling Regioselectivity in the Enantioselective N‐Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc‐ProPhenol

Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Enantioselective Friedel–Crafts Alkylation Reaction of Heteroarenes with N‐Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid

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