73698-07-4

Upstream product

• 58635-82-8 (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline 
• 928712-61-2 α-Hydroxy-4-methoxy-α-phenylbenzeneacetic acid methyl ester 
• 4254-17-5 4-methoxybenzoin 
• 63007-15-8 trans-(4S,5S)-2-benzoyl-4-(methoxymethyl)-5-phenyl-2-oxazoline 
• 73697-99-1 ((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-(4-methoxy-phenyl)-phenyl-methanol 
• 4237-50-7 4-methoxybenzilic acid 

Relevant academic research and scientific papers

Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes

Planar chiral 5,11-disubstiuted dibenzo[a,e]cyclo-octatetraenes (dbCOTs) have been developed as the first useful chiral homologs to dbCOT-ligands for asymmetric applications. Methods enabling the preparation of such compounds on a gram-scale in enantiomerically pure form are described. Evaluated as ligands in rhodium(I)-catalyzed 1,4- and 1,2-arylation reactions, tertiary and quarternary stereogenic centers were formed with excellent yields and selectivities of up to >99 % ee. A catalytic asymmetric synthesis of a key cyclization precursor to (?)-penifulvin A highlights the system in an applied context.

Asymmetric Addition of Organometallics to Chiral Ketooxazolines. Preparation of Enantiomerically Enriched α-Hydroxy Acids

Addition of Grignard and organolithium reagents to chiral α-ketooxazolines results in α-substituted α-hydroxyoxazoline derivatives which on hydrolytic removal of the chiral auxiliary groups give rise to α-substituted α-hydroxy acids in 30-87 percent enantiomeric excess (ee).Studies on the various parameters (solvents, temperature, substituents) were undertaken to reach optimum asymmetric induction.