215870-46-5

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 75-07-0 acetaldehyde 
• 215870-39-6 (R)-2-(3,4-Dimethoxy-benzylamino)-2-phenyl-ethanol 

Downstream Products

• 668446-50-2 (1R,2R)-2-[(3,4-dimethoxy-benzyl)-(1-methyl-3-phenyl-prop-2-ynyl)amino]-2-phenyl-ethanol 
• 306747-34-2 (1R,2R)-2-(1-methyl-3-phenyl-prop-2-ynylamino)-2-phenyl-ethanol 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines

Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 °C with dialkylalkynylalane-triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary α-substituted propargylamines can be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.

Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds

A new efficient and scalable route to chiral non-racemic α-substituted propargylamines is described. The reaction pathway consists of the diastereoselective addition of mixed alkynylaluminum reagents to oxazolidines derived from R- (-)-phenylglycinol.

Stereocontrolled addition of grignard reagents to chiral 1,3-oxazolidines having N-methoxybenzyl groups : Effect of N-substituent in diastereoselectivity

Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.