125151-82-8

Upstream product

• 100-52-7 benzaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 292638-85-8 acrylic acid methyl ester 
• 51608-60-7 phenyl N-tosyl imine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 203392-27-2 methyl 2-[fluoro(phenyl)methyl]acrylate 

Downstream Products

• 474744-52-0 Methyl 2-methyl-3-phenyl-3-(p-tolylsulfonylamino)propanoate 
• 807624-15-3 2-phenyl-1H-pyrrole-3-carboxylic acid 

Relevant academic research and scientific papers

Polymer-Supported Lewis Bases for the Baylis-Hillman Reaction

The use of polymer-supported Lewis bases such as PEG4600- (PPh2)2 and poly(DMAP) in the Baylis-Hillman reactions of N-tosylimines (ArCH=NTs) 1 or the corresponding arenecarbaldehydes with α,β-unsaturated ketones has been i

2-Phenyl-1 H-pyrrole-3-carboxamide as a New Scaffold for Developing 5-HT6Receptor Inverse Agonists with Cognition-Enhancing Activity

Serotonin type 6 receptor (5-HT6R) has gained particular interest as a promising target for treating cognitive deficits, given the positive effects of its antagonists in a wide range of memory impairment paradigms. Herein, we report on degradation of the

Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles

Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i

Aza-Morita-Baylis-Hillman reactions catalyzed by a cyclopropenylidene

Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles. Various aza-Morita-Baylis-Hillman reactions between aromatic, heteroaromatic, or aliphatic imines and acyclic or cyclic α,β-unsaturated ketones and carboxylic acid derivatives have been catalyzed by a BAC under mild conditions. Functionalities such as unprotected amino and hydroxy groups have been tolerated. The catalyst loading was decreased to 1 mol% without loss of activity. The BAC catalyst was shown to be substantially more active than a cyclic (alkyl)(amino) carbene (CAAC), N-heterocyclic carbenes (NHCs), and P- or N-centered Lewis bases.

Application of the ring-closing metathesis to the formation of 2-aryl-1H-pyrrole-3-carboxylates as building blocks for biologically active compounds

Ring-closing metathesis (RCM) is a powerful tool for the preparation of cyclic organic compounds. Yet, one of the major limitations of this method is the difficulty to prepare large quantities of target molecules. Herein we describe a comprehensive study

2-Trimethylsilylethanesulfonyl (SES) versus tosyl (Ts) protecting group in the preparation of nitrogen-containing five-membered rings. A novel route for the synthesis of substituted pyrrolines and pyrrolidines

(Chemical Equation Presented) The 2-trimethylsilylethanesulfonyl (or SES) protecting group was compared to the tosyl (Ts) group in the preparation of a nitrogen-containing five-membered ring obtained by the aza-Baylis - Hillman/alkylation/RCM route. While

Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis-Hillman catalysis: Synergistic effect of ionic liquids as organocatalyst supports

Hydroxyl ionic liquid (HIL) has been explored as a novel support for Baylis-Hillman catalyst. The HIL-supported catalyst showed a better catalytic activity compared to other IL-immobilized catalyst that has no hydroxyl group attached to the IL scaffold. T

Highly Efficient aza-Baylis-Hillman Reaction of N-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate: Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds

This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or α-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using

Sequential aza-Baylis-Hillman/ring closing metathesis/aromatization as a novel route for the synthesis of substituted pyrroles

A new route to diverse 2-substituted-3-methoxycarbonyl pyrroles has been developed. Diverse SES protected α-methylene β-aminoesters were obtained by a 3-component aza-Baylis-Hillman reaction. Diversity arose from the aryl aldehydes which can be used in th

Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction. Selective formation of α-methylene-β-amino acid derivatives

The direct formation of α-methylene-β-amino acid derivatives is achieved using the aza version of the Baylis-Hillman protocol. The products are readily formed in a three-component one-pot reaction between arylaldehydes, sulfonamides, and α,β-unsaturated c