Oxindole Amines from Isatin<sup>1</sup>

Conn, William R.; Lindwall, H. G.

doi:10.1021/ja01298a042

Cited by 22 publications

(14 citation statements)

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“…This additional ligand confers a higher stability to the complex, which is more easily handled with respect to complex 3. The effect of the copper complexation to the ligand is shown also by the 15 N NMR chemical shifts observed in CDCl 3 solution. For instance, the pyridine signal that resonates at 312 ppm in free ligand 1 is located at 248 ppm in complex 4.…”

Section: Resultsmentioning

confidence: 85%

“…[14] Encouraged by this result, we reacted isatine with nitroethane and a mixture of the diastereoisomers 6b in a ratio of 5:1 was obtained with an overall yield up to 80%. [15] Although this reaction opens up new routes for the synthesis of oxindole alkaloids, at the time we undertook our studies no reports on the diastereoselective nitroaldol reaction using isatine as substrate were available. Very recently, an excellent work by Wang and co-workers on the subject has been published.…”

Section: Resultsmentioning

confidence: 99%

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Henry reaction catalyzed by copper(I) complexes of a new pyridine‐containing macrocyclic ligand

Castano

Pedrazzini

Sisti

et al. 2011

Applied Organom Chemis

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The synthesis and characterization of copper(I) complexes of the novel pyridine-containing macrocyclic ligand (PC-L) and their use as catalysts in the Henry reaction are reported. The pyridine-based 12-membered tetraaza macrocyclic (PC-L) ligand 1 can be obtained in good overall yield (85%) from commercially available starting materials. The Cu(I) complexes showed good catalytic activities in the Henry reaction of different aldehydes and nitroalkanes. Remarkable diastereoselectivity was observed when isatine was reacted with nitroethane under catalytic conditions.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Henry reaction catalyzed by copper(I) complexes of a new pyridine‐containing macrocyclic ligand

Castano

Pedrazzini

Sisti

et al. 2011

Applied Organom Chemis

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“…M.p. 139 1418C [30,31] ; IR (KBR, cm . 5-Fluoro-3-hydroxy-3-(nitromethyl)indolin-2-one [42] (3b, Table 2, Entry 2): To a solution of isatin 1b (1.0 mmol) in freshly distilled DMF (3 mL) was added nitromethane (2 mmol) under nitrogen atmosphere.…”

Section: Discussionmentioning

confidence: 99%

“…This reaction has been utilized (30,31) for the synthesis of 3-hydroxy-3-(nitroalkyl)-oxindole by the reaction of nitoalkanes with isatins in presence of diethylamine (30) or alkali metal halides with electrochemical setup (31). Recently, catalystfree reactions have been attracting more and more attention from synthetic chemists (32Á39).…”

Section: Introductionmentioning

confidence: 99%

DMF mediated Henry reaction of isatins: an efficient synthesis of 3-hydroxy-2-oxindole

Meshram

Thakur

Bejjam

et al. 2013

Green Chemistry Letters and Reviews

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An efficient Henry reaction has been described for the synthesis of 3-hydroxy-3-(nitroalkyl)-2-oxindole by the reaction of isatins with nitroalkanes in N,N-dimethylformamide (DMF) under anhydrous condition. This method provides high yield of 3-hydroxy-2-oxindoles under mild reaction condition. Moreover, the procedure is environmentally benign in nature, efficient, and applicable to variety of isatins as well as nitroalkanes.

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“…The use of a-keto amides has not been reported to date, in fact, catalytic asymmetric intermolecular C À C bond formations with a-keto amides have so far been elusive. [6] We expected that careful reduction of the nitro group in a-hydroxy b-nitro propanamides would avoid problems with the facile retro-aldol reaction [7] and thus lead to a practical route to a series of chiral 1,3-diaminopropanols. [8] In recent years, chiral 1,3-oxazolidines have found increasing use as ligands and auxiliaries in asymmetric synthesis, which may be attributed to the intriguing ring topology and the possibility of modular synthesis from amino alcohols.…”

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confidence: 99%

Asymmetric Synthesis of Chiral 1,3‐Diaminopropanols: Bisoxazolidine‐Catalyzed CC Bond Formation with α‐Keto Amides

Wolf

2011

Angew Chem Int Ed

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The ever-increasing demand for enantiopure drugs and agrochemicals, and the use of chiral building blocks in polymers, liquid crystals, and other materials has generated a strong stimulus for the development of asymmetric methods that utilize previously unexplored starting materials to generate efficient access to new and emerging target compounds.[1] New drug candidates that bear a chiral 1,3-diaminopropanol moiety or a corresponding oxazolidinone derivative have recently been introduced for the treatment of tuberculosis, Alzheimers disease, and nosocomial infections caused by bacteria that are resistant to common antibiotics. [2] The formation of these challenging structures relies on multistep syntheses from chiral epoxy alcohols or esters and typically involves laborious protection/deprotection protocols. We envisioned that the enantioselective synthesis of Nsubstituted 1,3-diaminopropanols could be accomplished in three steps by nitroaldol reaction of a-keto amides, which are unexplored starting materials in asymmetric catalysis, and subsequent reduction of the nitro and amide groups (Scheme 1). The first catalytic asymmetric nitroaldol reaction was developed in 1992 by Shibasaki and coworkers, who used a BINOL-derived rare-earth-metal complex.[3] This reaction has since received considerable attention and its value for the synthesis of important chiral building blocks and complex target compounds has been demonstrated by many research groups.[4] Relatively few examples of asymmetric nitroaldol reactions with ketones [5] are known compared to the wealth of reactions with aldehydes. The use of a-keto amides has not been reported to date, in fact, catalytic asymmetric intermolecular C À C bond formations with a-keto amides have so far been elusive. [6] We expected that careful reduction of the nitro group in a-hydroxy b-nitro propanamides would avoid problems with the facile retro-aldol reaction [7] and thus lead to a practical route to a series of chiral 1,3-diaminopropanols. [8] In recent years, chiral 1,3-oxazolidines have found increasing use as ligands and auxiliaries in asymmetric synthesis, which may be attributed to the intriguing ring topology and the possibility of modular synthesis from amino alcohols.[9] We have previously introduced bisoxazolidine L1 and showed several applications of this C 2 -symmetric N,Odiketal in asymmetric catalysis (Scheme 2).[10] Despite the ease of preparation of L1, which can be obtained in a single step from inexpensive cis-1-amino-2-indanol and 1,2-cyclohexanedione, the synthesis of other diketone-derived bisoxazolidines is not straightforward and requires careful selection of starting materials and reaction conditions.[11] Accordingly, we chose to prepare a series of new ligands L2-L7 derived from (1R,2S)-aminoindanol analogues and several diketones to vary the rigidity of the N,O-diketal backbone and to explore the catalytic performance of fluxional bisoxazolidines in the nitroaldol reaction with keto amides.The synthesis of L2 started with the bromination of 1,2-...

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Oxindole Amines from Isatin¹

Cited by 22 publications

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Henry reaction catalyzed by copper(I) complexes of a new pyridine‐containing macrocyclic ligand

Henry reaction catalyzed by copper(I) complexes of a new pyridine‐containing macrocyclic ligand

DMF mediated Henry reaction of isatins: an efficient synthesis of 3-hydroxy-2-oxindole

Asymmetric Synthesis of Chiral 1,3‐Diaminopropanols: Bisoxazolidine‐Catalyzed CC Bond Formation with α‐Keto Amides

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Oxindole Amines from Isatin1

Cited by 22 publications

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Henry reaction catalyzed by copper(I) complexes of a new pyridine‐containing macrocyclic ligand

Henry reaction catalyzed by copper(I) complexes of a new pyridine‐containing macrocyclic ligand

DMF mediated Henry reaction of isatins: an efficient synthesis of 3-hydroxy-2-oxindole

Asymmetric Synthesis of Chiral 1,3‐Diaminopropanols: Bisoxazolidine‐Catalyzed CC Bond Formation with α‐Keto Amides

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Oxindole Amines from Isatin¹