Asymmetry

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers. Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity. (Wikipedia).

Enantioselective synthesis
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A Concise Enantioselective Total Synthesis of (–)-Deoxoapodine

An organic chemistry minilecture on A Concise Enantioselective Total Synthesis of (–)-Deoxoapodine by Kei Yoshida, Kosuke Okada, Hirofumi Ueda, and Hidetoshi Tokuyama*. Highlights include an enantioselective bromocycization, a Pd promoted C-H activation/alkylation cascade and an oxidative

From playlist Total Synthesis

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Nobel Prize in Chemistry 2021 Part 1, Asymmetric Organocatalysis, Enantioselective Organic Chemistry

An introduction to asymmetric catalysis, enantioselective reactions and asymmetric organocatalysis through a discussion of the proline catalysed aldol reaction. The video is pitched at an undergraduate chemistry level for those already familiar with general carbonyl reactivity in organic c

From playlist Nobel Prize Winning Chemistry

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Enantioselective Synthesis of (+)-Lucidumone

An organic chemistry minilecture on the Gram-Scale Enantioselective Synthesis of (+)-Lucidumone by Guanghao Huang, Cyrille Kouklovsky, and Aurélien de la Torre*. It features a highly stereoselective inverse electron demand Diels-Alder reaction, an unusual Mitsunobu reaction of a diketone a

From playlist Total Synthesis

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Enantioselective Total Synthesis of Cotylenin A Part Two

An organic chemistry minilecture on the Enantioselective Total Synthesis of Cotylenin A by Masahiro Uwamori, Ryunosuke Osada, Ryoji Sugiyama, Kotaro Nagatani, and Masahisa Nakada*. It features interesting protecting group manipulation, and acetalization-epoxide-opening cascade sequence and

From playlist Total Synthesis

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Total Synthesis of ent-Plagiochianin B

An organic chemistry minilecture on the Total Synthesis of ent-Plagiochianin B by Richard K. Jackson III and John L. Wood*. It features a creative azatriene electrocyclization pyridine synthesis, an exo-alkene selective palladium catalysed oxidation and an endo-alkene selective iron catal

From playlist Total Synthesis

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Retrosynthesis 9 - Organic Chemistry

Retrosynthetic analysis of a spirocyclic unsaturated ketone to showcase 1,6-diX disconnections and the pinacol rearrangement as synthesis strategies in organic chemistry. More retrosynthesis videos here: https://www.youtube.com/watch?v=lD02HC4h6yw&list=PLavaRHHaRimVhyZD79H8g08cfhxrZMcB1 #

From playlist Retrosynthesis

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Imine and Enamine Formation Reactions With Reductive Amination

This organic chemistry video tutorial provides a basic introduction into imines and enamines. An imine can form in the reaction of a ketone with a primary amine and enamine can be produced by mixing a ketone with a secondary amine. The imine and enamine can be reduced to amines by reduct

From playlist New Organic Chemistry Playlist

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Rings and Retrosynthesis for this Natural Product - Organic Chemistry

A classical disconnection approach to the retrosynthesis of racemic mesembrine, showcasing an intramolecular Mannich reaction, enolate chemistry, Michael additions and decarboxylation strategies. #chemistry #organicchemistry #orgo #ochem #education #science #stem # This natural product h

From playlist Retrosynthesis

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Synthesis Workshop: Enantioselective Synthesis of Ammonium Cations with Dr. Mark Walsh (Episode 73)

In this Research Spotlight episode, we're joined by Dr. Mark Walsh, who takes us through his work on the enantioselective synthesis of ammonium cations (Kitching group, Durham University). The modules featured in this episode were nominated for C&EN magazine's Molecule of the Year: https:

From playlist Research Spotlights

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CCHF VS 13.1 - Prof. Olivier Baudoin

Prof. Olivier Baudoin, from University of Basel, speaks on Pd0-catalyzed enantioselective C(sp3)-H activation.

From playlist CCHF Virtual Symposia

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Five Important Papers in Organic Synthesis (December 2022)

Download ReactionFlash for free using the following links: Apple App Store: https://apps.apple.com/app/apple-store/id432080813?pt=119296909&ct=ThatChemist-Ad3&mt=8 Google Play Store: https://play.google.com/store/apps/details?id=ch.reaxys.reactionflash&hl=en_GB&gl=US&utm_campaign=reaction

From playlist Important Papers

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Synthesis Workshop: Enantioselective Intermolecular Amination with Alexander Fanourakis (Episode 80)

In this Research Spotlight episode, we're joined by Alexander Fanourakis, who shares with us his work on enantioselective intermolecular amination using chiral cations. Key reference: J. Am. Chem. Soc. 2021, 143, 10070-10076. https://doi.org/10.1021/jacs.1c05206 Other references (in orde

From playlist Special Topics: Organometallics

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A C−H Functionalization Strategy Enables an Enantioselective Formal Synthesis of (−)-Aflatoxin B2

An organic chemistry minilecture on the paper 'A C−H Functionalization Strategy Enables an Enantioselective Formal Synthesis of (−)-Aflatoxin B2' by Nicholas A. Falcone, Aaron T. Bosse, Hojoon Park, Jin-Quan Yu, Huw M. L. Davies* and Erik J. Sorensen*. Highlights include a Rh-promoted C-H

From playlist Total Synthesis

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Synthesis Workshop: Enantioselective 1,2-Boronate Rearrangements with Dr. Hayden Sharma (Episode 81)

In this Research Spotlight episode, Dr. Hayden Sharma joins us to share his work on enantioselective, catalytic 1,2-boronate rearrangements, which was carried out in the Jacobsen lab at Harvard. Key paper: Science 2021, 374, 752–757. https://doi.org/10.1126/science.abm0386 Other referenc

From playlist Special Topics: Organocatalysis

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Synthesis Workshop: Total Synthesis of Leucophyllidine with Dr. Aurapat Ngamnithiporn (Episode 64)

In this Research Spotlight episode, we're joined by Dr. Aurapat (Fa) Ngamnithiporn, who shares with us her work on the enantioselective synthesis of eburnamonine, eucophylline, and 16’-epi-leucophyllidine. Key reference: Angew. Chem. Int. Ed. 2021, 60, 17957-17962. https://doi.org/10.1002

From playlist Research Spotlights

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Synthesis Workshop: Asymmetric Hydrogenation of Oximes with Dr. Josep Mas-Roselló (Episode 23)

In this Research Spotlight episode, Dr. Josep Mas-Roselló joins us to talk about his recently published work on the asymmetric hydrogenation of oximes in the Cramer group. Parent reference: Science 2020, 368, 1098-1102. Other references (in order of appearance): ‘The Chemistry of Hydroxy

From playlist Special Topics: Organometallics

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Enantioselective Total Synthesis of Cotylenin A- Part One

An organic chemistry minilecture on the Enantioselective Total Synthesis of Cotylenin A by Masahiro Uwamori, Ryunosuke Osada, Ryoji Sugiyama, Kotaro Nagatani, and Masahisa Nakada*. It features an interesting Catalytic Asymmetric Intramolecular Cyclopropanation, Utimoto coupling, Takai reac

From playlist Total Synthesis

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Synthesis of (±)-Lysergic Acid

An organic chemistry minilecture on the 'Six-Step Synthesis of (±)-Lysergic Acid' by Brian J. Knight, Ryan C. Harbit, and Joel M. Smith*. It demonstrates a short, modular synthesis that can be used to synthesize analogues of LSD using a reductive dearomatization and an intramolecular Heck

From playlist Total Synthesis

Related pages

Europium | Homochirality | Asymmetric induction | Noyori asymmetric hydrogenation | Thalidomide | Osmium tetroxide | Entropy | Amino acid | Chirality (chemistry) | Asymmetric hydrogenation