178237-98-4

Upstream product

• 591-51-5 phenyllithium 
• 178237-95-1 (4S)-4-methyl-3-N-(9'-phenylfluoren-9'-yl)oxazolidin-5-one 
• 108-86-1 bromobenzene 
• 105519-71-9 (S)-N-[9-(9-phenylfluorenyl)]alanine 

Downstream Products

• 178238-03-4 (1R,2S)-1-phenyl-2-[N-(9'-phenylfluoren-9'-yl)amino]propan-1-ol 
• 178238-01-2 (1S,2S)-1-phenyl-2-[N-(9'-phenylfluoren-9'-yl)amino]propan-1-ol 

Relevant academic research and scientific papers

Enantiospecific Synthesis of N-9-Phenylfluoren-9-yl-α-amino Ketones

Enantiomerically pure N-(9-phenylfluoren-9-yl)-α-amino ketones were prepared in excellent yields by acylation of organolithium reagents with N-(9-phenylfluoren-9-yl)-α-amino acid-derived oxazolidinones. The method is not applicable for the acylation of Grignard reagents as they attack the methylenic carbon of the oxazolidinone to give the corresponding N-alkylated amino acids 13 in excellent yields. The resulting N-(9-phenylfluoren-9-yl)-α-amino ketones 8 could be stereoselectively reduced to the corresponding syn- or anti-β-amino alcohols depending upon the nature of the reducing agent.

Enantiospecific synthesis of α-amino ketones and β-amino alcohols from the reaction of N-(9-phenylfluoren-9-yl)-alanine oxazolidinone with organolithium reagents

Enantiomerically pure N-(9-phenylfluoren-9-yl) α-amino ketones were prepared by reaction of the N-Pf-alanine-derived oxazolidinone with organolithium reagents. α-Amino ketones thus obtained could be stereoselectively reduced to the corresponding syn or anti β-amino alcohols depending upon the nature of the reducing agent.