Organocatalytic Enantioselective Mannich Reaction: Direct Access to Chiral β-Amino Esters

Kumar, Gulshan; Ramesh, B.; Yarlagadda, Suresh; Sridhar, Balasubramanian; Reddy, B. V. Subba

doi:10.1021/acsomega.8b02132

Cited by 14 publications

(9 citation statements)

References 68 publications

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“…The solid was filtered and washed with H 2 O and ether. The resulting white solid was dried under reduced pressure to give 2.62 g (6.4 mmol, 58%) of tert -butyl [3,4-dimethoxyphenyl(phenylsulfonyl)methyl]carbamate ( 1m ), which is a known compound , without spectral data. Mp: 152–154 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of N-Boc-α-amino Acids from Carbon Dioxide by Electrochemical Carboxylation of N-Boc-α-aminosulfones

et al. 2021

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Electrochemical reduction of N-Boc-α-aminosulfones in DMF using an undivided cell equipped with a Pt plate cathode and an Mg rod anode under atmospheric pressure of bubbling carbon dioxide through the solution under constant current conditions resulted in a reductive C–S bond cleavage with elimination of benzenesulfinate ion generating the corresponding anion species followed by fixation of carbon dioxide to give the corresponding N-Boc-α-amino acids in moderate to good yields.

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Section: Methodsmentioning

confidence: 99%

Synthesis of N-Boc-α-amino Acids from Carbon Dioxide by Electrochemical Carboxylation of N-Boc-α-aminosulfones

et al. 2021

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“…Fascinatingly, the aldimines obtained from heteroaromatic aldehydes afforded the corresponding products in excellent yield and ee s (Scheme 47). [83] …”

Section: Organocatalyzed Asymmetric Mannich Reactionmentioning

confidence: 99%

Organocatalyzed Asymmetric Mannich Reaction: An Update

et al. 2021

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The Mannich reaction is a multicomponent reaction resulting in aminoalkylation of an acidic proton placed next to a carbonyl functional group. It involves an appropriate carbonyl compound, such as formaldehyde and a primary or secondary amine or ammonia. The final product is a β‐amino‐carbonyl compound known as a Mannich base. Reactions between aldimines and α‐methylene carbonyls are also considered as Mannich reaction since these imines are generated from the reaction of amines and aldehydes. It comprises the reaction of primary or secondary amines or ammonia, formaldehyde and appropriate α‐CH‐acidic compounds (nucleophiles) such as carbonyl compounds having α‐CH‐acidic, nitriles, acetylenes, aliphatic nitro compounds, α‐alkyl‐pyridines or imines. Owing to the development of asymmetric organocatalysis, reports on asymmetric Mannich reaction have been drastically increased. The asymmetric Mannich reaction offers access to enantioenriched β‐amino ketones or β‐amino aldehydes, which are present as a scaffold in several natural products. Organocatalysts have been developed not only as a supplement to metal‐catalyzed reactions or to biocatalysis, but nowadays, they are extensively used for the synthesis of various optically pure compounds that could not be achieved via metal‐ or biocatalyzed reactions. In this review, we try to update the advances in organocatalyzed asymmetric Mannich reactions, covering the recent advances of the subject from 2008 to date.

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“…Bifunctional thiourea systems were employed to the reaction between 3-indolinone-2carboxylates 58 to N-Boc-benzaldimines generated in situ from α-amidosulfones 59 [61]. The best results in terms of chemical yield, enantio-and diastereoselectivity were obtained with the use of thiourea 60 (Scheme 22) [61]. Chiral derivatives of isatins occur in the nature; these are compounds such as (+)-isatisine A, trigonoliimine or mersicarpine.…”

Section: Asymmetric Mannich Reactionsmentioning

confidence: 99%

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

2021

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The main purpose of this review article is to present selected asymmetric synthesis reactions in which chemical and stereochemical outcomes are dependent on the use of an appropriate chiral catalyst. Optically pure or enantiomerically enriched products of such transformations may find further applications in various fields. Among an extremely wide variety of asymmetric reactions catalyzed by chiral systems, we are interested in: asymmetric cyclopropanation, Friedel–Crafts reaction, Mannich and Michael reaction, and other stereoselective processes conducted in the presence of zinc ions. This paper describes the achievements of the above-mentioned asymmetric transformations in the last three years. The choice of reactions is related to the research that has been carried out in our laboratory for many years.

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Organocatalytic Enantioselective Mannich Reaction: Direct Access to Chiral β-Amino Esters

Cited by 14 publications

References 68 publications

Synthesis of N-Boc-α-amino Acids from Carbon Dioxide by Electrochemical Carboxylation of N-Boc-α-aminosulfones

Synthesis of N-Boc-α-amino Acids from Carbon Dioxide by Electrochemical Carboxylation of N-Boc-α-aminosulfones

Organocatalyzed Asymmetric Mannich Reaction: An Update

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

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