682352-13-2

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 682352-10-9 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 476431-61-5 (1S,2R,6S)-9,9-dimethyl-4-oxa-5-thiatricyclo[6.1.1.0^2,6]decane 5-oxide 
• 444308-38-7 {(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol 
• 444308-41-2 (1S,2R,5R,7S)-5-acetyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 444308-42-3 (1S,2R,5R,7S)-5-[(R)-1'-hydroxy-1'-phenyl-1'-ethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 599192-45-7 (1S,2R,5R,7S,9R)-5-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 599192-60-6 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylethyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 858658-58-9 bis-[(1S,2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,6-dimethyl-bicyclo[3.1.1]hept-3-yl] disulfide 
• 682352-20-1 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-19-8 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-12-1 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-11-0 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-08-5 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 

Downstream Products

• 858658-57-8 (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.0^2,7]undecane 
• 3966-31-2 (R)-2-hydroxy-2-phenylbutyric acid 
• 682352-08-5 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 
• 682352-09-6 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 
• 682352-10-9 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-11-0 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-12-1 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-19-8 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-20-1 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 21504-01-8 (R)-2-hydroxy-2-phenylbutanal 
• 858658-58-9 bis-[(1S,2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,6-dimethyl-bicyclo[3.1.1]hept-3-yl] disulfide 
• 2404-42-4 (S)-(-)-2-phenyl-butane-1,2-diol 

Relevant academic research and scientific papers

Enantioselective synthesis of either enantiomer of α-alkyl-α- hydroxy-α-phenylacetic acids using chiral auxiliaries

The enantioselective synthesis of either enantiomer of α-alkyl- α-hydroxy-α-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee).

New S,O-acetals from (1R)-(-)-myrtenal as chiral auxiliaries in nucleophilic additions

Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99% yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er).