1541176-83-3

Upstream product

• 1541176-80-0 (+)-(S)-2-methyl-N-[(3S,4R)-1-tosyl-4-{1-(trimethylstannyl)vinyl}pyrrolidin-3-yl]propane-2-sulfinamide 
• 420132-18-9 N-(buta-2,3-dien-1-yl)-4-methyl-N-(2-oxoethyl)benzenesulfonamide 
• 1353342-73-0 (+)-(S)-N-(buta-2,3-dienyl)-N-{2-(tert-butylsulfinylimino)ethyl}-4-methylbenzenesulfonamide 

Downstream Products

• 1541176-89-9 (-)-(S)-2-methyl-N-{(3S,4R)-4-(4-methylpenta-1,4-dien-2-yl)-1-tosylpyrrolidin-3-yl}propane-2-sulfinamide 

Relevant academic research and scientific papers

Regulation of diastereoselectivity in the carbocyclization of allenyl (S)-N-tert-butylsulfinimines through a three-component assembly

Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (S)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B- bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.