175229-12-6

Upstream product

• 100-39-0 benzyl bromide 
• 116611-44-0 ((R)-2-benzenesulfonyl-1-hydroxymethyl-ethyl)carbamic acid tert-butyl ester 
• 218933-98-3 (2R,2'S)-3-benzyloxy-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]propyl phenyl sulfone 
• 121911-32-8 1-[(E)-3-(benzyloxy)prop-1-enylsulfonyl]benzene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 220047-55-2 (R)-2-amino-3-benzyloxypropyl phenyl sulfone 

Downstream Products

• 220047-55-2 (R)-2-amino-3-benzyloxypropyl phenyl sulfone 
• 253776-40-8 (2R,5S)-3-Benzenesulfonyl-2,5-bis-benzyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 188401-92-5 (2S,5S)-2,5-bis(benzyloxymethyl)pyrrolidine 
• 126550-74-1 (2R,5S)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-benzyloxymethylpyrrolidine 
• 212266-70-1 Toluene-4-sulfonic acid (S)-3-[((R)-2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-2-hydroxy-propyl ester 
• 212266-68-7 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine 
• 212266-69-8 (S)-3-[((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-propane-1,2-diol 
• 220047-69-8 (2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 220047-66-5 ((3R,4S,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol 
• 220047-97-2 (2R,3S,4R)-3-Benzenesulfonyl-2,4-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 212266-65-4 (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-hydroxymethylpyrrolidine 
• 220047-60-9 Toluene-4-sulfonic acid (S)-3-[((R)-2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-tert-butoxycarbonyl-amino]-2-hydroxy-propyl ester 
• 220047-59-6 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,3-dihydroxy-propyl)-carbamic acid tert-butyl ester 
• 220047-71-2 (2S,4R)-2-Benzyloxymethyl-4-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of α-substituted β-amino sulfones by aza-Michael addition to alkenyl sulfones and subsequent α-alkylation

The aza-Michael addition of enantiopure 1-aminopyrrolidines to (E)- alkenyl sulfones in the presence of a catalytic amount of ytterbium trifluoromethanesulfonate [Yb(OTf)3] yields β-hydrazino sulfones in moderate to good yields and with diastereoselectivities of up to 98%. The latter undergo reductive N-N bond cleavage with BH3 · THF and, after N- protection with Boc2O or benzyl bromide, afford N-protected β-amino sulfones with moderate to high enantiomeric excesses (ee = 42 to ≥96%) without racemization. Subsequent α-alkylation of the N,N-dibenzyl protected β-amino sulfones with various electrophiles yields α-alkyl-β-amino sulfones in excellent yields (88-97%) with high diastereomeric (de ≥96 to ≥98%) and enantiomeric purity (ee = 94 to ≥96%). The absolute configuration of the new stereogenic centre was determined by X-ray structural analysis and confirmed by NMR spectroscopy (NOE experiments). Possible reaction mechanisms for the conjugate addition and α-alkylation are presented.

Efficient N-N bond cleavage of chiral trisubstituted hydrazines with BH3·THF

Cleavage of the N-N bond of chiral trisubstituted hydrazines 1 with excess BH3·THF complex gives the corresponding optically active amines 2 in moderate to excellent yields and with high enantiomeric purity. This racemization and epimerization free cleavage procedure is compatible with functionalities sensitive to reductive cleavage conditions.

Versatile synthesis of enantiomerically pure trans-2,5-disubstituted pyrrolidines

Enantiomerically pure trans-(2S,5S)-2,5-disubstituted pyrrolidine was synthesized starting from the versatile chiral synthon (R)-(8) and chiral 2,3-O-isopropylideneglycerol triflate (S)-(9).