87481-06-9

Upstream product

• 2259-30-5 tert-butylmagnesium bromide 
• 87443-40-1 1-[2-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-ethanone 
• 676-58-4 methylmagnesium chloride 
• 87443-42-3 1-[2-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-2,2-dimethyl-propan-1-one 
• 598-98-1 Methyl pivalate 
• 51594-34-4 (1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol 
• 77250-60-3 (4S,5S)-2-(2-bromophenyl)-4-methoxymethyl-5-phenyl-2-oxazine 

Relevant academic research and scientific papers

AN ASYMMETRIC SYNTHESIS OF CHIRAL PHTHALIDES VIA CHIRAL LITHIATED OXAZOLINES

Chiral aromatic oxazolines were prepared for utilization in asymmetric C-C bonding reactions.Lithiation of aryloxazolines could not be accomplished directly but were efficiently lithiated via halogen metal exchange of the o-bromo derivative (16).The resulting lithio compound (9) reacted smoothly with carbonyls to give adducts 19 but with poor stereoselectivity.Hydrolysis gave the phthalides 4 in poor ee's (20-25percent).When the lithio-oxazolines 9 were transformed into 21, they now served as chiral electrophiles.Addition of organometallics to 21 gave, particularly with Grignard reagents, useful levels of asymmetric induction which, after hydrolysis, gave phthalides 4 in 40-80percent ee.