256382-83-9

Upstream product

• 1146970-49-1 1-(((2R,5R)-5-butyl-1-tosylpyrrolidin-2-yl)methoxy)-2,2,6,6-tetramethylpiperidine 
• 1324003-99-7 (R)-4-methyl-N-(non-1-en-5-yl)benzenesulfonamide 
• 256382-82-8 (2R,5R)-2-(hydroxymethyl)-5-butyl-N-(p-tosyl)-pyrrolidine 

Downstream Products

• 256382-85-1 (2R,5S)-2-Butyl-1-(toluene-4-sulfonyl)-5-[3-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-propyl]-pyrrolidine 
• 256382-84-0 (2R,5R)-2-Butyl-1-(toluene-4-sulfonyl)-5-[(Z)-3-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-propenyl]-pyrrolidine 

Relevant academic research and scientific papers

Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols

A new method for the direct conversion of 4-pentenylsulfonamides to 2-formylpyrrolidines and a 2-ketopyrrolidine has been developed. This transformation occurs via aerobic copper-catalyzed alkene aminooxygenation where molecular oxygen serves as both oxidant and oxygen source. The 2-formylpyrrolidines can further undergo oxidative carbon-carbon bond cleavage in situ upon addition of DABCO, providing 2-pyrrolidinones. These transformations have been demonstrated for a range of 4-pentenylsulfonamides. 4-Pentenylalcohols also undergo oxidative cyclization to form γ-lactones predominantly. The reaction is chemoselective, oxidizing one alkene in the presence of others, and is compatible with several functional groups. Application of these reactions to the formal syntheses of baclofen and (+)-monomorine was demonstrated.

Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: Formal synthesis of (+)-monomorine

The diastereoselectivity of the copper-promoted intramolecular aminooxygenation of various alkene substrates was investigated. a-Substituted 4-pentenyl sulfonamides favor the formation of 2,5-c/s-pyrrolidines (dr > 20:1) giving excellent yields which range from 76-97% while y-substituted substrates favor the 2,3-trans pyrrolidine adducts with moderate selectivity (ca. 3:1). A substrate whose N-substituent was directly tethered to the a-carbon exclusively yielded the 2,5-trans pyrrolidine. The synthetic utility of the method was demonstrated by a short and efficient formal synthesis of (+)-monomorine.

A general approach to indolizidine alkaloids from 1-benzyloxy-5-(p- toluenesulfonamido)-3-alken-2-ols: Synthesis of (+)-monomorine I

A versatile method for the preparation of indolizidine alkaloids from 1- benzyloxy-5-(p-toluenesulfonamido)-3-alken-2-ols as stereodefined key intermediates has been developed. The utility of this approach was demonstrated by the synthesis of (+)-monomori