212071-06-2

Upstream product

• 816457-76-8 methyl 2-((N-allyl-2-(trimethylsilyl)ethan-3-ylsulfonamido)(phenyl)methyl)acrylate 
• 100-52-7 benzaldehyde 
• 125486-96-6 2-(trimethylsilyl)ethanesulfonamide 
• 816457-61-1 methyl 2-(phenyl(2-(trimethylsilyl)ethylsulfonamido)methyl)acrylate 
• 18913-35-4 methyl buta-2,3-dienoate 

Downstream Products

• 52179-69-8 methyl 2-phenyl-1H-pyrrole-3-carboxylate 
• 3042-22-6 2-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

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

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

A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin

The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates 2-butynoates with an appropriate phosphine as the catalyst, toward the electron-deficient imines is described. Triphenylphosphine-catalyzed reaction of methyl 2,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.