Convenient one-pot synthesis of 4,8-dimethyl-bicyclo[3.3.1)non-7-en-2-ol via platinum/tin catalyzed hydroformylation/cyclization of limonene

Article abstract of DOI:10.1016/S0040-4039(96)02251-4

Limonene (1) was converted in one step into two diastereoisomers of 4,8-dimethyl-bicyclo[3.3.1]non-7-en-2-ol (2), useful as perfumes, employing PtCl₂(PPh₃)₂/PPh₃/SnCl₂ and PtCl₂(diphosphine)/PPh₃/SnCl₂ systems as bifunctional catalysts whose diphosphines were 1,3-bis(diphenylphosphino)propane (dppp) and 1,4-bis(diphenylphosphino)butane (dppb). In the presence of the PtCl₂(dppb)/PPh₃/SnCl₂ system, which was found to be the most promising combination, the selectivity for 2 reached the value of 82% at 95% conversion of 1.