183201-36-7

Upstream product

• 109-72-8 n-butyllithium 
• 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 
• 6175-45-7 2,2-diethoxyacetophenone 
• 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 
• 20826-80-6 2-phenylhex-1-ene 

Relevant academic research and scientific papers

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).