212195-40-9

Upstream product

• 212195-32-9 3-Biphenyl-4-yl-3-(tert-butyl-dimethyl-silanyloxy)-2-diallylamino-propionic acid methyl ester 
• 212195-34-1 1-Biphenyl-4-yl-2-diallylamino-propane-1,3-diol 
• 212195-36-3 (4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-amine 
• 3218-36-8 4-Phenylbenzaldehyde 
• 101293-94-1 methyl rac-2-amino-3-(biphenyl-4-yl)-3-hydroxypropanoate 
• 518358-60-6 N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]propane-1-sulfonamide 
• 74-88-4 methyl iodide 

Downstream Products

• 212195-45-4 (R)-1-Phenyl-butane-2-sulfonic acid ((4S,5S)-4-biphenyl-4-yl-2,2-dimethyl-[1,3]dioxan-5-yl)-methyl-amide 
• 212195-44-3 (3R)-N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylheptane-3-sulfonamide 

Relevant academic research and scientific papers

Asymmetric synthesis of α-substituted N-methylsulfonamides

A novel amine auxiliary for the asymmetric synthesis of α-substituted N-methylsulfonamides is described. The reaction of 4-([1,1′-biphenyl]-4-yl)-2,2-dimethyl-1,3-dioxan-5-amine (16) with various aliphatic sulfonyl chlorides afforded the corresponding sulfonamides, which were lithiated and subsequently reacted with electrophiles to give the corresponding products in high yields and good-to-excellent asymmetric inductions (de 83-95%). Racemization-free cleavage of the auxiliary led to the α-alkylated N-methylsulfonamides in acceptable yields and high enantiomer purities (ee 91 to ≥ 98).

Enantioselective synthesis of α-substituted N-methyl-sulfonamides

The first asymmetric α-alkylations of lithiated sulfonamides bearing the chirality information within the amine moiety under high asymmetric inductions (de 83-95 %) are described. Racemization-free acidic hydrolysis led to the title compounds 11 in acceptable overall yields and with high enantiomeric purity (ee 91- ≤98%; Scheme 2). As a novel chiral auxiliary, the primary amine (S,S)- or (R,R)-2 was synthesized employing the classical Erlenmeyer phenylserine synthesis (Schone I).