InCl<sub>3</sub>-Catalyzed Three-Component Asymmetric Mannich-Type Reaction in Methanol

Loh, Teck‐Peng; Chen, Shui‐Ling

doi:10.1021/ol0265968

Cited by 87 publications

(19 citation statements)

References 11 publications

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“…One can see that in a blank run the isolated yield of b-amino carbonyl compound is only 8%. Over C 6 [28], InCl 3 [29], Y(OTf) 3 [30], Yb(OPf) 3 (Ytterbium perfluorooctanoate) [ [38] and Bi(OTf) 3 [39] were used as catalysts in the Mannich-type reactions. Despite individual feature(s) and/or merit(s) of the catalysts, drawbacks such as difficulty of product separation, impossible recycling and reuse of catalyst caused much concerns.…”

Section: H 11 N(c 6 H 4 ) 2 Bi(oso 2 C 8 F 17 )-Catalyzed Mannichmentioning

confidence: 99%

Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

Zhang

Yin

Qiu

et al. 2009

Journal of Organometallic Chemistry

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Section: H 11 N(c 6 H 4 ) 2 Bi(oso 2 C 8 F 17 )-Catalyzed Mannichmentioning

confidence: 99%

Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

Zhang

Yin

Qiu

et al. 2009

Journal of Organometallic Chemistry

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“…The sterically demanding isopropyl group selectively shields the Re face of the imine derivative, and the nucleophilic addition thus takes place on the Si face. [52] InCl 3 was recycled and reused without any loss of activity.…”

Section: Diastereoselective Approachmentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

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“…Traditional catalysts for direct Mannich reactions of aldehydes, ketones and amines involve mainly Lewis or Brønsted acids (Loh et al, 2000;Akiyama et al, 2001;Manabe et al, 2001;Loh & Chen, 2002;Phukan et al, 2006;Yang et al, 2006). However, the use of these catalysts is followed by a number of serious disadvantages.…”

Section: Introductionmentioning

confidence: 99%

Formation of a vanillic Mannich base – theoretical study

et al. 2015

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One-pot anti-Mannich reaction of vanillin, aniline and cyclohexanone was successfully catalyzed by ionic liquid triethanolammonium chloroacetate, at room temperature. Yield of the obtained Mannich base was very good and excellent diastereoselectivity was achieved. Mechanism of the reaction was investigated using the density functional theory. The reaction started with a nucleophilic attack of aniline nitrogen at the carbonyl group of vanillin. The intermediate α-amino alcohol formed in this way was further subjected to protonation by the triethanolammonium ion yielding the imminium ion. Theoretically, the obtained imminium ion and the enol form of cyclohexanone can build the protonated Mannich base via the anti and syn pathways. The chloroacetic anion spontaneously abstracts the proton yielding the final product of the reaction anti 2-[1-(N-phenylamino)-1-(4-hydroxy-3-methoxyphenyl)]methylcyclohexanone (MB-H). The syn pathway requires lower activation energy but the anti pathway yields a thermodynamically more stable product, which implies that the examined Mannich reaction is thermodynamically controlled.

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InCl₃-Catalyzed Three-Component Asymmetric Mannich-Type Reaction in Methanol

Abstract: [reaction: see text] A one-pot InCl(3)-catalyzed Mannich-type reaction was carried out in methanol. High diastereoselectivities and high yields were obtained. In addition, after the reaction was completed, InCl(3) can be recycled and reused without a drop of activity and selectivity.

Cited by 87 publications

References 11 publications

Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Formation of a vanillic Mannich base – theoretical study

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InCl3-Catalyzed Three-Component Asymmetric Mannich-Type Reaction in Methanol

Abstract: [reaction: see text] A one-pot InCl(3)-catalyzed Mannich-type reaction was carried out in methanol. High diastereoselectivities and high yields were obtained. In addition, after the reaction was completed, InCl(3) can be recycled and reused without a drop of activity and selectivity.

Cited by 87 publications

References 11 publications

Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Formation of a vanillic Mannich base – theoretical study

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InCl₃-Catalyzed Three-Component Asymmetric Mannich-Type Reaction in Methanol