115156-63-3

Upstream product

• 73698-01-8 ((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-naphthalen-1-yl-phenyl-methanol 
• 1074-12-0 phenylglyoxal hydrate 
• 63007-15-8 trans-(4S,5S)-2-benzoyl-4-(methoxymethyl)-5-phenyl-2-oxazoline 
• 58635-82-8 (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline 
• 115156-57-5 (2S,4aS,7R,8aR)-2-benzoyl-N-benzyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 703-55-9 1-naphthylmagnesiumbromide 
• 18434-67-8 O-(naphthyl-⁽¹⁾-oxoacetyl)-(1R)-menthol 

Relevant academic research and scientific papers

HIGHLY ENANTIOSELECTIVE SYNTHESES OF α-HYDROXYACIDS USING N-BENZYL-4,4,7α-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE AS A CHIRAL ADJUVANT

Addition of Grignard and organolithium reagents to as well as hydride reduction of 2α-benzoyl-N-benzyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (2, Y = C6H5CO) and addition of phenylmagnesium bromide to the corresponding 2-acetyl analog (11) proceed in highly diastereoselective fashion to produce virrtually exclusively the diastereomer predicted on the basis of Cram's chelate rule if chelation involves the ring oxygen atom.Mild acid hydrolysis of the adducts followed by selective oxidation produces highly enantiomerically pure α-hydroxyacids with clean recovery of the chiral adjuvant.

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.