222733-19-9

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 120417-13-2 (S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 13398-53-3 (S)-α-methylphenylglycinol 
• 222733-14-4 (S,S)-2-(2-methoxy-1-methyl-1-phenylethylamino)-2-phenylethanol 

Relevant academic research and scientific papers

Highly diastereoselective addition of Grignard reagents to aliphatic, enolizable N-alkylketimines and 2,2-disubstituted 1,3-oxazolidines. Asymmetric synthesis of the antidepressant cericlamine

Grignard reagents were added to 2,2-disubstituted 1,3-oxazolidines and enolizable ketimines prepared from hydroxyacetone and phenylglycinol derivatives, with high to excellent diastereoselectivity, to yield 2,2- disubstituted 1,2-amino alcohol derivatives. Lewis acids had considerable influence on the yield and diastereoselectivity of the addition. This method was applied to the first asymmetric synthesis of the 5-HT reuptake inhibitor Cericlamine.