87481-07-0

Upstream product

• 676-58-4 methylmagnesium chloride 
• 87443-55-8 (5S)-2-(benzoyl)phenyl-5-phenyl-2-oxazoline 
• 87443-43-4 [2-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-phenyl-methanone 
• 87443-40-1 1-[2-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-ethanone 
• 77250-60-3 (4S,5S)-2-(2-bromophenyl)-4-methoxymethyl-5-phenyl-2-oxazine 
• 98-86-2 acetophenone 
• 93-89-0 benzoic acid ethyl ester 
• 51594-34-4 (1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 87443-39-8 (S)-2,5-diphenyl-1,3-oxazoline 

Downstream Products

• 87443-52-5 (R)-3-Methyl-3-phenyl-3H-isobenzofuran-1-one 

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.