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Kinetic evidence for a tetrameric transition state in the asymmetric autocatalytic alkylation of pyrimidyl aldehydes.
TLDR
Experimental kinetic data coupled with kinetic modeling reveal the Soai reaction to be an example of true autocatalytic efficiency in a template-directed "minimal system" for self-replication.
Efficient Iron‐Catalyzed Kumada Cross‐Coupling Reactions Utilizing Flow Technology under Low Catalyst Loadings
An efficient continuous flow iron-catalyzed Kumada cross-coupling was developed for the coupling of 2-chloropyrazine and various aryl Grignard reagents in presence of low catalyst loadings (0.5
Transnitrilation from Dimethylmalononitrile to Aryl Grignard and Lithium Reagents: A Practical Method for Aryl Nitrile Synthesis.
TLDR
An electrophilic cyanation of aryl Grignard or lithium reagents by a transnitrilation with dimethylmalononitrile (DMMN) was developed and supported the energetic favorability of retro-Thorpe fragmentation of the imine adduct.
Insights into palladium-catalyzed cyanation of bromobenzene: additive effects on the rate-limiting step.
TLDR
This work demonstrates that the addition of a catalytic amount of ZnBr(2) facilitates the reaction with an elimination of the induction period observed without additive, allowing a qualitative assessment of the effect of water on the rate-limiting step and the apparent reaction order in bromobenzene.
Synthesis of the 6-azaindole containing HIV-1 attachment inhibitor pro-drug, BMS-663068.
TLDR
The synthesis leverages an unusual heterocyclic N-oxide α-bromination to functionalize a critical C-H bond, enabling a highly regioselective copper-mediated Ullmann-Goldberg-Buchwald coupling to install a challenging triazole substituent.
Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.
TLDR
A concise asymmetric synthesis of an 11β-HSD-1 inhibitor has been achieved using inexpensive starting materials with excellent step-economy at low catalyst loadings using a unique P,N-ligand with 1000 ppm of [Ir(COD)Cl]2.
Development of a concise, scalable synthesis of a CCR1 antagonist utilizing a continuous flow Curtius rearrangement
TLDR
A convergent, robust, and concise synthesis of a developmental CCR1 antagonist is described using continuous flow technology and the resulting API synthesis is determined to be extremely green relative to the industrial average for molecules of similar complexity.
Development of Multikilogram Continuous Flow Cyclopropanation of N-Benzylmaleimide through Kinetic Analysis
A convenient and high-yielding method for the synthesis of trans-(dioxo)-azabicyclo-[3.1.0]-hexane carboxylate, a key intermediate of complex molecules, is presented using a flow cyclopropanation
Mechanistic insight into the palladium-catalyzed 1,4-oxidation of 1,3-dienes to 1,4-dicarboxy-alk-2-enes.
TLDR
During the course of this investigation, several previously unreported kinetic phenomena were observed and gave a greater understanding of the mechanism of this transformation and led to the discovery of a new, highly active palladium complex for diene oxidation.
Development of a Scalable, Chromatography-Free Synthesis of t-Bu-SMS-Phos and Application to the Synthesis of an Important Chiral CF3-Alcohol Derivative with High Enantioselectivity Using
TLDR
A chromatography-free, asymmetric synthesis of the C2-symmetric P-chiral diphosphine t-Bu-SMS-Phos was developed using a chiral auxiliary-based approach using an air-stable crystalline form of the final ligand to enable isolation of thefinal ligand by crystallization to avoid chromatography.
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