Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

Hong, Bor‐Cherng; Raja, Arun; Sheth, Vishal M.

doi:10.1055/s-0035-1560344

Cited by 72 publications

(17 citation statements)

References 65 publications

(68 reference statements)

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“…These reactions, in which a generated intermediate spontaneously undergoes further (often intramolecular) transformations without adding fresh reagents and/or a catalyst, are commonly less material‐ and energy‐consuming than sequences of corresponding reactions performed separately, which makes them perspective in terms of green chemistry . In particular, domino reactions significantly simplify a multi‐step syntheses of valuable natural compounds and enantiomerically pure medications …”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

et al. 2018

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The most recyclable ionic liquid‐supported bifunctional tertiary amine–squaramide organocatalyst for the asymmetric domino reaction has been found. Over this catalyst, ortho‐aminochalcones protected with Tosyl or Nosyl groups underwent the aza‐Michael/Michael domino reaction with nitroolefins to afford corresponding 2,3,4‐trisubstituted tetrahydroquinolines as single diastereomers in nearly quantitative yield with up to 99 % ee. The catalyst was readily separated from the reaction mixture via a simple centrifugation/decantation workup and 19 times reused in the catalytic reaction without noticeable conversion or enantioselectivity reduction. The N‐nosylated products proved their synthetic value for pharmacology given their facile conversion to fused pirrolidino‐tetrahydroquinolines of high diastreomeric and enantiomeric purity via successive deprotection and reductive amination.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

et al. 2018

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“…[1][2][3][4][5] In this context the resurgent use of coinage metals as catalysts in organic synthesis has received much attention, and has resulted in the development of a wide range of gold-catalysed reactions. [6][7][8][9][10][11] Even though in many cases the nature of the active catalytic species involved in these transformations has yet to be resolved, as has a full description of the mechanistic pathways of the reactions concerned.…”

Section: Introductionmentioning

confidence: 99%

Some insights into the gold-catalysed A 3 -coupling reaction

Price

Brisdon

Randall

et al. 2017

Journal of Organometallic Chemistry

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Abstract.A series of cyclometallated and functionalised NHC gold(I) and gold(III) complexes, many of which feature chiral ligands, and their application to A 3 -coupling reactions is presented. Gold(III) complexes were found to be particularly effective catalysts for the coupling in a range of solvents, however no asymmetric induction was obtained when using chiral gold complexes and the rate of product formation was found to be similar even when using different ligand systems. In-situ NMR analysis of these reactions indicates that decomposition of the catalyst occurs during the course of the reaction while TEM studies revealed the presence of gold nanoparticles in crude reaction mixtures. Taken together these data suggest that the gold nanoparticales, rather than the intact gold complexes, could be the catalytically active species, and if so this may have significant implications for other gold-catalysed systems.Dedicated to Dr. Mark Whiteley (an outstanding colleague) on his retirement from the School of Chemistry, University of Manchester.

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“…This can be achieved by using different chiral catalysts, via asymmetric catalyzed reactions. 1 The development of asymmetric synthesis is very important in those parts of industry, which are engaged with the mass production of some useful natural products such as amino acids. 2 Asymmetric synthesis is a key step in modern organic chemistry and is vital in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activities and in some cases while one of them is remedial, the opposite stereoisomer is devastating.…”

Section: Introductionmentioning

confidence: 99%

“…Ar = 2-MeC 6 H 4 , yield = 99%, ee = >99.5% 246o: Ar = 4-MeOC 6 H 4 , yield = 97%, ee = 99% 246p: Ar = benzo[d][1,3]dioxole, yield = 99%, ee = 99% 246q: Ar = 4-Me 2 NC 6 H 4 , yield = 97%, ee = 97% 246r: Ar = naphthalene, yield = 94%, ee = 99% 246s: Ar = 4-FC 6 H 4 , yield = 97%, ee = >99.5% 246t: Ar = 4-ClC 6 H 4 , yield = 96%, ee = >99.5% 246u: Ar = 3,4-Cl 2 C 6 H 3 , yield = 94%, ee = >99.5% 246v: Ar = 4-CF 3 C 6 H 4 , yield = 96%, ee = >99.5%Scheme 124. Rhodium-catalyzed stereoselective addition of arylboronic acids 2 to 245b.…”

mentioning

confidence: 99%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

107

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

Cited by 72 publications

References 65 publications

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

Some insights into the gold-catalysed A 3 -coupling reaction

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

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