249622-08-0

Upstream product

• 1082828-67-8 C₂₆H₃₁NO₂ 

Downstream Products

• 249622-10-4 (-)-(1R,2R)-2-N,N-dimethylamino-1-isopropylaminocarbonylmethoxy-1,2-diphenylethane 
• 596799-68-7 (1R,2R)-2,4-dimethyl-3-pentyl 2-(2-dimethylamino-1,2-diphenylethoxy)benzoate 
• 249622-09-1 (-)-(1R,2R)-2-N,N-dimethylamino-1-ethoxycarbonylmethoxy-1,2-diphenylethane 

Relevant academic research and scientific papers

Chiral anion-mediated asymmetric ring opening of meso-aziridinium and episulfonium ions

Reactions proceeding through cationic intermediates that lack a Lewis or Bronsted basic site present a challenge for traditional asymmetric catalysis based on chiral metals or organocatalysts. We present an enantioselective ring opening of tetrasubstituted meso-aziridinium ions with alcohol nucleophiles proceeding through a chiral ion pair with a binaphthol-phosphate anion. The reaction is initiated by silver-induced ring closure of β-chloroamines using the Ag salt of the chiral anion as in situ generated catalyst. Use of insoluble Ag2CO3 as silver source is essential to obtain high enantioselectivity; we believe the chiral phosphate acts as a chiral anion phase transfer catalyst to bring silver ion into the organic phase. The chiral anion concept can also be extended to the related asymmetric opening of meso-episulfonium ions generated by protonation of trichloroacetimidates vicinal to sulfides. Copyright