104197-95-7

Upstream product

• 65253-04-5 (-)-8-phenylmenthol 
• 129180-87-6 Phenyl-carbamic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 100101-42-6 (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 
• 57707-91-2 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 
• 129180-90-1 (+)-8-phenylisomenthyl bromoacetate 
• 129180-87-6 Phenyl-carbamic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 104870-80-6 (1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 
• 129180-92-3 (-)-8-phenylneoisomenthyl bromoacetate 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 
• 129180-87-6 (-)-8-phenylmenthol phenylcarbamate 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 

Downstream Products

• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 108794-01-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate 
• 108793-98-2 (-)-8-phenylmenthyl (2S)-2-hydroxyoctanoate 
• 108793-97-1 (-)-8-phenylmenthyl (2S)-2-hydroxy-2-cyclohexylacetate 
• 100020-76-6 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate 
• 108793-99-3 (-)-8-phenylmenthyl (2S,3S)-2-hydroxy-3-isopropyl-4-pentenoate 
• 108794-06-5 (2'S)-3'-(cyclohex-1-enyl)-2'-hydroxy-propionic acid (1R,2S,5R)-8-phenylmenthyl ester 
• 108793-96-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-2-(2-cyclohexenyl)acetate 
• 108794-03-2 (-)-8-phenylmenthyl (2S)-2-hydroxy-6-acetoxy-4-hexenoate 
• 108794-07-6 (-)-8-phenylmenthyl (2S)-2-hydroxy-3-(4-t-butyl-1-cyclohexenyl)propionate 
• 108794-09-8 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-(2-acetoxyethyl)-4-pentenoate 
• 108794-05-4 (-)-8-phenylmenthyl (2S)-2-hydroxy-6-(t-butyldimethylsiloxy)-4-hexenoate 
• 108794-04-3 (-)-8-phenylmenthyl (2S)-2-hydroxy-6-benzyloxy-4-hexenoate 
• 88112-35-0 (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-3-methyl-4-pentenoate 

Relevant academic research and scientific papers

ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY PURE S-ISOSERINE

KF-promoted addition of nitromethane on (-)-8-phenylmethyl glyoxylate monohydrate affords, after one purification, optically pure (-)S isoserine in about 50percent yield.

C- and N-Selective Grignard Addition Reactions of α-Aldimino Esters in the Presence or Absence of Zinc(II) Chloride: Synthetic Applications to Optically Active Azacycles

Highly practical synthetic methods were developed for the C- and N-selective Grignard addition reactions of N-4-MeOC6H4-protected α-aldimino esters in the presence or absence of zinc(II) chloride. Diastereoselective C-alkyl addition, tandem C-alkyl addition-N-alkylation, and some transformations to synthetically useful optically active azacycles were demonstrated. (Chemical Equation Presented).

PREPARATION OF THREE DIASTEREOISOMERS OF 2-(1-METHYL-1-PHENYLETHYL)-5-METHYLCYCLOHEXAN-1-OL FROM (R)-(+)-PULEGONE

New isolation of (1R,2S,5R)-(-)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexan-1-ol ((-)-8-phenylmenthol, Ia), prepared from (R)-(+)-pulegone, is described.The method consists in the preparation of phenylcarbamate of Ia and its transesterification with ethanol.Further two diastereoisomers of (-)-8-phenylmenthol were isolated: the (1S,2R,5R)-isomer IIa and the (1R,2R,5R)-isomer IIIa.Compounds Ia, IIa and IIIa were converted into their respective glyoxylates Ic, IIc and IIIc.

ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL

We recently communicated (J.K.Whitesell, A.Bhattacharya, D.A.Aguilar and K.Henke, J.Chem.Soc.Chem.Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes.We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety of situations that warrants a more complete presentation of these reactions.