Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors

Bandini, Marco; Garelli, Andrea; Rovinetti, Matteo; Tommasi, Simona; Umani‐Ronchi, Achille

doi:10.1002/chir.20189

Cited by 69 publications

(46 citation statements)

References 61 publications

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“…(61)] gave a (+)-NLE, thus suggesting the involvement of dimeric or oligomeric complexes. [164] Earlier studies [ 165] 3. Homogeneous Organocatalytic Reactions…”

Section: Miscellaneous Reactionsmentioning

confidence: 98%

Nonlinear Effects in Asymmetric Catalysis

Satyanarayana¹,

Abraham²,

Kagan³

2008

Angew Chem Int Ed

500

273

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There is a need for the preparation of enantiomerically pure compounds for various applications. An efficient approach to achieve this goal is asymmetric catalysis. The chiral catalyst is usually prepared from a chiral auxiliary, which itself is derived from a natural product or by resolution of a racemic precursor. The use of non-enantiopure chiral auxiliaries in asymmetric catalysis seems unattractive to preparative chemists, since the anticipated enantiomeric excess (ee) of the reaction product should be proportional to the ee value of the chiral auxiliary (linearity). In fact, some deviation from linearity may arise. Such nonlinear effects can be rich in mechanistic information and can be synthetically useful (asymmetric amplification). This Review documents the advances made during the last decade in the use of nonlinear effects in the area of organometallic and organic catalysis.

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“…(61)] gave a (+)-NLE, thus suggesting the involvement of dimeric or oligomeric complexes. [164] Earlier studies [ 165] 3. Homogeneous Organocatalytic Reactions…”

Section: Miscellaneous Reactionsmentioning

confidence: 98%

Nonlinear Effects in Asymmetric Catalysis

Satyanarayana¹,

Abraham²,

Kagan³

2008

Angew Chem Int Ed

500

273

View full text Add to dashboard Cite

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“…[11,12] Recently, nitroalkenes have been used extensively as substrates in the asymmetric Friedel-Crafts alkylation of indoles. [13,14] The nitro group is one of the strongest electron-withdrawing groups known, so nitroalkenes have proven excellent Michael acceptors. [15] This, coupled with the fact that the nitro group is easily transformed into a range of different functionalities, has resulted in their wide application in organic synthesis.…”

Section: Friedel-crafts Catalysismentioning

confidence: 99%

New Thiazoline–Oxazoline Ligands and Their Application in the Asymmetric Friedel–Crafts Reaction

2009

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Six members of a novel non‐C2‐symmetric ligand class incorporating an oxazoline and thiazoline unit have been prepared in a four‐step, high‐yielding and convergent synthesis, in which the key step is a microwave‐assisted palladium‐catalyzed aryl amination. The new ligands induced enantiomeric excesses of up to 76 % in the asymmetric Friedel–Crafts reaction.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…The nitroolefins are recognized as excellent Michael aceptors 48,49 and their derivatives are important intermediates in organic synthesis due to the synthetic versatility of the nitro-group as precursor of other organic functionalities. [50][51][52] First, we investigated the reaction of indole 1a wiyh nitrostyrene 4a carried out under the reactions conditions described above (i-PrOH, room temperature and 10 mol% of SnCl 2 ·2H 2 O).…”

Section: Reactions Of Indoles With Nitrostyrenesmentioning

confidence: 99%

Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins

Schwalm¹,

Ceschi²,

Russowsky³

2011

J. Braz. Chem. Soc.

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O were investigated as mild Lewis acids catalysts for the conjugate Friedel-Crafts reaction between indoles and activated olefins. The reactions were carried out with aliphatic unsaturated ketones over a period of days at room temperature, while chalcones reacted only under reflux conditions. The reactions with nitrostyrenes were either performed in solvent or under solventless conditions. In all cases reasonable to good yields were obtained.

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Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors

Cited by 69 publications

References 61 publications

Nonlinear Effects in Asymmetric Catalysis

Nonlinear Effects in Asymmetric Catalysis

New Thiazoline–Oxazoline Ligands and Their Application in the Asymmetric Friedel–Crafts Reaction

Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins

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