953395-23-8

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 615-36-1 2-bromoaniline 
• 1024-38-0 N-(2-bromophenyl)-4-methylbenzenesulfonamide 
• 16088-62-3 (S)-Propylene oxide 
• 953395-21-6 (2S)-1-[2-(4-methylphenylsulfonamido)phenyl]-2-propanyl 3-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]acetate 

Downstream Products

• 953395-24-9 (S)-1-(2-(4-methylphenylsulfonamido)phenyl)-2-propanyl 4-pentynoate 
• 953395-26-1 (S)-1-(2-(4-methylphenylsulfonamido)phenyl)-2-propanyl 2-ethynylbenzoate 

Relevant academic research and scientific papers

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Catalytic activation of the leaving group in the SN2 reaction

A novel catalytic activation of the leaving group in the SN2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)2 to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S N2 reaction. The procedure is applicable for benzoazepine synthesis.