152983-53-4

Upstream product

• 849596-44-7 [1S-(1α,2α,3β,4β)]-cyclohexane-1,2,3,4-tetrol 
• 108-24-7 acetic anhydride 
• 215026-14-5 (1S,2S,1'S)-2-(cyclohex-2'-enyloxy)-1,2-diphenylethanol 
• 215026-15-6 (1S,3S,4S,6S,7S)-3,4-diphenyl-7-phenylseleno-2,5-dioxabicyclo[4,4,0]decane 
• 849596-43-6 (1S,3S,4S,6R,7S,8S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]decane-7,8-diol 
• 849596-42-5 (1S,3S,4S,6R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-7-ene 
• 1521-51-3 rac-3-bromocyclohexene 

Relevant academic research and scientific papers

Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources

Reaction of 3-bromocyclohexene with (S,S)-hydrobenzoin and (S)-mandelic acid and subsequent intramolecular oxyselenenylation of the resulting allylic ethers followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefins, (1S,3S,4S,6R)-3,4-diphenylbicyclo[4,4,0]-2,5-dioxa-7-decene and (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxan-2-one, respectively. Further stereoselective transformation of these cis-fused bicyclic olefins afforded the enantiopure cyclohexitols, muco-quercitol, D-chiro-inocitol and allo-inocitol.

Transformation of cyclohexene to enantiopure cyclitols mediated by sequential oxyselenenylation with (S,S)-hydrobenzoin: Synthesis of D-chiro-inositol and muco-quercitol

Oxyselenenylation of cyclohexene with (S,S)-hydrobenzoin and subsequent oxidation-elimination allows isolation of an allylic ether in which further phenylselenenylation is completely regioselective, thus allowing entry to the cyclitols D-chiro-inositol and muco-quercitol.