Asymmetric Synthesis of Tetrahydroisoquinoline Alkaloids Using Ellman's Chiral Auxiliary

Reddy, Y. V. R.; Biradar, Dhanraj O.; Reddy, B. Jagannadha; Rathod, Aravinda; Himabindu, M.; Reddya, B. V. Subba

doi:10.1177/1934578x1701201019

Cited by 3 publications

(3 citation statements)

References 44 publications

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“…As a very important class of natural products, tetrahydroisoquinoline alkaloids are widely distributed in nature with various structures (Figure 1) [1][2][3][4][5] . Among these compounds, tetrahydroisoquinoline has been identified as their central framework, and this heterocyclic system is of strategic importance in many research and industrial fields.…”

Section: Introductionmentioning

confidence: 99%

Convenient synthesis of 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitriles via a cascade Michael/cyclization reaction

Wang

Chen

Guo

et al. 2022

J Chinese Chemical Soc

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A convenient and straightforward cascade Michael/cyclization reaction of 1‐alkylpiperidin‐4‐ones, acyl acetonitriles, and aldehydes was proposed for the construction of significant 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitriles promoted by DBU, and various 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitrile derivatives were produced in medium to high yields. The methodology features a simple operation process, accessible raw material, and high atomic economy.

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Section: Introductionmentioning

confidence: 99%

Convenient synthesis of 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitriles via a cascade Michael/cyclization reaction

Wang

Chen

Guo

et al. 2022

J Chinese Chemical Soc

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“…Due to the pharmacological importance of THIQs, many synthetic methods have been developed, such as the Bischler-Napieralski reaction, 264 Pictet-Spengler reaction, 265 Pomeranz-Fritsch reaction, 266,267 and haloamide cyclization (Figure 4-2). 268 The Bischler-Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction of β-arylethylamide to form dihydroisoquinolines, from which further reduction leads to THIQs. The Pomeranz-Fritsch reaction is an acid promoted condensation of benzaldehyde and 2,2-dialkoxyethylamine for isoquinoline synthesis.…”

Section: General Methods To Construct Tetrahydroisoquinolinesmentioning

confidence: 99%

“…Haloamide cyclizations are usually used in the asymmetric synthesis of THIQs, with the chiral center (C1) built before ring formation. 268,269 Among all the above-mentioned reactions, the Pictet-Spengler reaction constructs the THIQ core in one step with diversified aldehyde or ketone monomers, which makes it widely used in THIQ synthesis.…”

Section: General Methods To Construct Tetrahydroisoquinolinesmentioning

confidence: 99%

Efforts to expand chemistry toolbox for DNA-encoded libraries

Jaturapitakkul¹

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List of SchemesChapter 2: Threonine Aldolase Catalyzed on-DNA Aldol Reaction………………………………..…48 Scheme 2-1. (a) Retro-aldol cleavage of threonine, (b) Threonine aldolase catalyzed aldol reaction, and (c) Catalytic cycle……………………………………………………………………………………………….50 Scheme 2-2. Hypothesis on reactivity loss of HP-1c and HP-1m…………………………………………..56 Scheme 2-3. Diversification of β-hydroxy-α-amino acids…………………………………………………..63 Scheme 2-4. Two proposed libraries…………………………………………………………………………64 Chapter 3: on-DNA Macrocyclization Utilizing Intramolecular Benzimidazole Formation………66 Scheme 3-1. Proof of concept tests…………………………………………………………………………..73 Scheme 3-2. Reaction scheme for scoping study…………………………………………………………...74 Scheme 3-3. Optimized on-DNA nitro reduction…………………………………………………………….76 Scheme 3-4. Proposed Libraries……………………………………………………………………………...77 Scheme 3-5. Acid-aldehyde 3-step validation……………………………………………………………….79 Scheme 3-6. Library scheme………………………………………………………………………………….82 Chapter 4: on-DNA Tetrahydroisoquinoline Formation via Pictet-Spengler Reaction……………89 Scheme 4-1. Pictet-Spengler reactions and reaction mechanism…………………………………………90 Scheme 4-2. on-DNA Pictet-Spengler reaction with CjNCS2………………………………………………92 Scheme 4-3. Proposed catalytic pathway of phosphate catalyzed PS reaction………………………….93 Scheme 4-4. Acylation and reductive acylation of the secondary amine………………………………...108 Scheme 4-5. Fluorosulfonate formation and coupling reactions………………………………………….109 Scheme 4-6. Synthetic scheme of potential DELs…………………………………………………………111

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N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

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Asymmetric Synthesis of Tetrahydroisoquinoline Alkaloids Using Ellman's Chiral Auxiliary

Cited by 3 publications

References 44 publications

Convenient synthesis of 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitriles via a cascade Michael/cyclization reaction

Convenient synthesis of 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitriles via a cascade Michael/cyclization reaction

Efforts to expand chemistry toolbox for DNA-encoded libraries

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

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