Introduction of cis-vicinal amino alcohol functionality into the cyclohexane ring employing (1S,2S)-2-amino-1,2-diphenylethanol: Synthesis of enantiopure aminocyclohexitols

Article abstract of DOI:10.1016/S0957-4166(01)00484-0

Pd(0)-catalyzed allylic amination of 3-bromocyclohexene with (1S,2S)-2-amino-1,2-diphenylethanol and subsequent intramolecular oxyselenenylation of the resulting allylic amine 6 followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefin 10. Oxyselenenylation of cyclohexene with (1S,2S)-N-(benzyloxycarbonyl)-2-amino-1,2-diphenylethanol and subsequent oxidation-elimination gave the allylic ether 18. Intramolecular aminoselenenylation of 18 followed by oxidation-elimination provided the cis-fused bicyclic olefin 21, which is the regioisomer of 10. Further stereoselective transformation of 10 afforded enantiopure aminocyclohexitols.