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Organocatalysis

ACh cover 24/2003The term organocatalysis describes the acceleration of chemical reactions through the addition of a substoichiometric quantity of an organic compound. The interest in this field has increased spectacularly in the last few years as result of both the novelty of the concept and, more importantly, the fact that the efficiency and selectivity of many organocatalytic reactions meet the standards of established organic reactions. Organocatalytic reactions are becoming powerful tools in the construction of complex molecular skeletons.[1,2]

[1] P. I. Dalko, L. Moisan,
Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726
Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138.

[2] Special issue of Adv. Synth. Catal. 2004, 346, Nr. 9-10.

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Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes

Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes

[Communication]
Mélanie Decostanzi, Jérémy Godemert, Sylvain Oudeyer, Vincent Levacher, Jean-Marc Campagne, Eric Leclerc
Adv. Synth. Catal., February 9, 2016, DOI: 10.1002/adsc.201500849. Read article.

Enantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues

Enantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues

From Supersilyl to Super Killers: Enantiopure monomeric nuphar alkaloids having apoptotic activity were discovered (see example), and concise enantioselective formal syntheses of 11 nuphar alkaloids were achieved. The syntheses featured the unprecedented use of supersilyl groups to control the regio-, diastereo-, and enantioselectivity of vinylogous Mukaiyama–Mannich reactions.

[Communication]
Hui Li, Alexander Korotkov, Charles W. Chapman, Alan Eastman, Jimmy Wu
Angew. Chem. Int. Ed., February 05, 2016, DOI: 10.1002/anie.201600106. Read article

Protonated Phosphazenes: Structures and Hydrogen-Bonding Organocatalysts for Carbonyl Bond Activation

Protonated Phosphazenes: Structures and Hydrogen-Bonding Organocatalysts for Carbonyl Bond Activation

[Full Paper]
Damien Jardel, Clotilde Davies, Frédéric Peruch, Stéphane Massip, Brigitte Bibal
Adv. Synth. Catal., February 4, 2016, DOI: 10.1002/adsc.201600062. Read article.

Bifunctional Brønsted Base Catalyzes Direct Asymmetric Aldol Reaction of α-Keto Amides

Bifunctional Brønsted Base Catalyzes Direct Asymmetric Aldol Reaction of α‐Keto Amides

New players in town: The enantioselective direct cross-aldol reaction of α-keto amides with aldehydes was accomplished using ureidopeptide-based Brønsted base catalysts. The reaction provides stereodefined syn-aldol adducts without self-condensation, competitive aldehyde enolization, aldol dehydration, and lactonization products, which are usually observed when using α-keto esters as donor partners. Cbz=benzyloxycarbonyl.

[Communication]
Haizea Echave, Rosa López, Claudio Palomo
Angew. Chem. Int. Ed., February 02, 2016, DOI: 10.1002/anie.201510482. Read article

Asymmetric α-Hydroxylation of β-Indanone Esters and β-Indanone Amides Catalyzed by C-2' Substituted Cinchona Alkaloid Derivatives

Asymmetric α-Hydroxylation of β-Indanone Esters and β-Indanone Amides Catalyzed by C-2' Substituted Cinchona Alkaloid Derivatives

[Full Paper]
Yakun Wang, Hang Yin, Hai Qing, Jingnan Zhao, Yufeng Wu, Qingwei Meng
Adv. Synth. Catal., January 26, 2016, DOI: 10.1002/adsc.201500911. Read article.

Guerbet Alcohols: From Processes under Harsh Conditions to Synthesis at Room Temperature under Ambient Pressure

Guerbet Alcohols: From Processes under Harsh Conditions to Synthesis at Room Temperature under Ambient Pressure

Fantastic four: The synthesis of Guerbet alcohols at room temperature under ambient pressure is reported; this is in contrast to today's industrial production, which is performed under harsh reaction conditions. The presented process is based on the combination of two organocatalytic steps with a biocatalytic two-step tandem process starting from readily available aliphatic alcohols. High conversions and selectivities are found for all steps.

[Communication]
Marc Biermann, Hendrik Gruß, Werner Hummel, Harald Gröger
ChemCatChem, January 26, 2016, DOI: 10.1002/cctc.201501241. Read article

Synthesis of (+)-trans-Dihydrolycoricidine by an Organocatalytic Enantioselective Friedel–Crafts Reaction

Synthesis of (+)‐trans‐Dihydrolycoricidine by an Organocatalytic Enantioselective Friedel–Crafts Reaction

Organocatalyzed FC: Enantioselective synthesis of antitumor alkaloid, trans-dihydrolycoricidine, was achieved by means of a 1,4-type Friedel–Crafts reaction by using a guanidine/bisthioure organocatalyst, followed by an intramolecular Henry reaction for construction of the C ring system.

[Full Paper]
Masaru Kato, Koji Yasui, Masahiro Yamanaka, Kazuo Nagasawa
Asian J. Org. Chem., January 22, 2016, DOI: 10.1002/ajoc.201500469. Read article

Novel Base-Free Catalytic Wittig Reaction for the Synthesis of Highly Functionalized Alkenes

Novel Base-Free Catalytic Wittig Reaction for the Synthesis of Highly Functionalized Alkenes

Drop the base: A novel catalytic system based on a readily available phosphine oxide precatalyst for base-free catalytic Wittig reactions has been developed (see scheme). Under the optimized reaction conditions, numerous functionalized alkenes were prepared in yields up to 99 % and with good to excellent E/Z selectivities.

[Full Paper]
Marie-Luis Schirmer, Sven Adomeit, Anke Spannenberg, Thomas Werner
Chem. Eur. J., January 13, 2016, DOI: 10.1002/chem.201503744. Read article.

Covalently Supported Ionic Liquid Phases: An Advanced Class of Recyclable Catalytic Systems

Covalently Supported Ionic Liquid Phases: An Advanced Class of Recyclable Catalytic Systems

Multitasking catalytic materials: Covalently supported ionic liquid phases (cSILP) are useful catalytic materials for many organic transformations. This Review takes a look at the most recent advances in the synthesis and catalytic applications of cSILP.

[Review]
Francesco Giacalone, Michelangelo Gruttadauria
ChemCatChem, January 13, 2016, DOI: 10.1002/cctc.201501086. Read article

Catalysts Encapsulated in Molecular Machines

Catalysts Encapsulated in Molecular Machines

Incorporating control: The unique stimulus-responsive feature of molecular machines endows traditional catalysts with dynamic properties. Molecular switches, rotaxanes, and motors are utilized as scaffolds to construct switchable, stereoselective, and processive catalysts (see figure).

[Minireview]
Tiezheng Pan, Junqiu Liu
ChemPhysChem, January 11, 2016, DOI: 10.1002/cphc.201501063. Read article

The First Enantioselective Organocatalytic Synthesis of 3-Spiro-α-Alkylidene-γ-Butyrolactone Oxindoles

The First Enantioselective Organocatalytic Synthesis of 3-Spiro-α-Alkylidene-γ-Butyrolactone Oxindoles

An innovative and flexible methodology catalyzed by bifunctional chiral thioureas was developed to react β-nitro oxindoles with aldehydes (see scheme). This approach allows the first enantioselective synthesis of 3-spiro-α-alkylidene-γ-butyrolactone oxindoles 3 with the aim of merging two potentially bioactive structural motifs: the spirooxindole and the α-alkylidene-γ-butyrolactone.

[Full Paper]
Lucia Cerisoli, Marco Lombardo, Claudio Trombini, Arianna Quintavalla
Chem. Eur. J., January 7, 2016, DOI: 10.1002/chem.201504157. Read article.

Chiral Triazoles in Anion-Binding Catalysis: New Entry to Enantioselective Reissert-Type Reactions

Chiral Triazoles in Anion-Binding Catalysis: New Entry to Enantioselective Reissert-Type Reactions

Against the elements: A family of chiral triazoles has been introduced as innovative C-H bond-based hydrogen donors for anion-binding catalysis. Contrary to the believed inefficiency of the low polarized C-H bonds for promoting organocatalysis, these structures proved to be competitive with respect to the more established N-H-type hydrogen donors in enantioselective Reissert-type reactions.

[Full Paper]
Mercedes Zurro, Sören Asmus, Julia Bamberger, Stephan Beckendorf, Olga García Mancheño
Chem. Eur. J., January 7, 2016, DOI: 10.1002/chem.201504094. Read article.

Deep Eutectic Solvents for Organocatalysis, Biotransformations, and Multistep Organocatalyst/Enzyme Combinations

Deep Eutectic Solvents for Organocatalysis, Biotransformations, and Multistep Organocatalyst/Enzyme Combinations

Solvents to provide solutions: the application of deep eutectic solvents (DES) in different areas, such as biotransformations, organocatalysis, and combinations of these that lead to multistep processes, is discussed. DES can be used as solvents, cosolvents, performance additives for bio- and organocatalysis, tools to anchor organocatalysts selectively, or for extraction/separation.

[Minireview]
Nadia Guajardo, Christoph R. Müller, Rodrigo Schrebler, Carlos Carlesi, Pablo Domínguez de María
ChemCatChem, December 23, 2015, DOI: 10.1002/cctc.201501133. Read article

Acetaldehyde: A Small Organic Molecule with Big Impact on Organocatalytic Reactions

Acetaldehyde: A Small Organic Molecule with Big Impact on Organocatalytic Reactions

Utility of acetaldehyde: Acetaldehyde has recently received a great deal of attention as the simplest enolizable carbonyl compound because of its versatile applications in the synthesis of poly(vinyl alcohol), unnatural amino acids, and medicine (see graphic). This Minireview summarizes a methodologically diverse approach to the synthesis of target molecules by outlining a diverse array of reactions such as aldol, Mannich, Michael, and NHC-catalyzed reactions.

[Minireview]
Sun Min Kim, Young Sug Kim, Dong Wan Kim, Ramon Rios, Jung Woon Yang
Chem. Eur. J., December 15, 2015, DOI: 10.1002/chem.201503960. Read article.

The Resurgence of the Highly Ylidic N-Heterocyclic Olefins as a New Class of Organocatalysts

The Resurgence of the Highly Ylidic N-Heterocyclic Olefins as a New Class of Organocatalysts

One carbon better: N-Heterocyclic olefins, the alkylidene derivatives of the prevalent N-heterocyclic carbenes, have recently emerged as efficient promoters for CO2 fixation and polymerization reactions. Their extraordinarily strong Lewis/Brønsted basicity suggests great potential as a new class of organocatalysts for a broad range of reactions in synthetic chemistry.

[Concept]
Reece D. Crocker, Thanh V. Nguyen
Chem. Eur. J., November 26, 2015, DOI: 10.1002/chem.201503575. Read article.

Whither Organic Synthesis?

Whither Organic Synthesis?

[Review]
Douglass F. Taber
Isr. J. Chem., April 15, 2015, DOI: 10.1002/ijch.201500006. Read article

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