573701-29-8

Upstream product

• 100-52-7 benzaldehyde 
• 143394-39-2 (S)-(+)-2-(N-methylamino)-2-phenylethanol 
• 225645-17-0 (2S)-N-benzyl-N-methyl-2-phenylglycine methyl ester 
• 135357-90-3 (2R)-N-benzyl-2-amino-2-phenyl-1-ethanol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1161829-01-1 [N(R)]-N-allyl-N-benzyl-N-[(1S)-2-hydroxy-1-phenylethyl]-N-methylammonium bromide 
• 1161828-92-7 [N(S)]-N-allyl-N-benzyl-N-[(1S)-2-hydroxy-1-phenylethyl]-N-methylammonium bromide 
• 28102-51-4 (4S*)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri

'N-stereogenic quaternary ammonium salts' from L-amino acids: Synthesis, separation, and absolute configuration

Diastereoisomeric linear and cyclic 'N-chiral quaternary ammonium salts' (QASs) were efficiently synthesized from corresponding L-amino acids in high yields. The diastereoisomers of each pair of 'N-chiral QASs' were successfully separated. The absolute configurations of these QASs were determined predominately by X-ray single-crystal analysis. The 1H-NMR data of 'N-chiral QASs' provided characteristic information on the configuration of the N-chiral center. 'N-Chiral QASs' exemplified by [N(R)]-2a and [N(S)]-2a are stable in protic and aprotic solvents within a broad pH and temperature range.

Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids

Amino diazoacetoacetates 4a-e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c-e furnished the morpholin-2-ones 5c-e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion. Cyclic substrates 7a,b underwent conversion to bicyclic morpholinones 8 and 9 in good yield and with moderate to good diastereoselectivity. This result is rationalized via control of the transiently stereogenic ammonium center of the intermediate bicyclic ylides.