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

doi:10.1016/S0040-4039(96)02251-4

Tetrahedron Letters

Volume 38, Issue 1, 6 January 1997, Pages 41-44

https://doi.org/10.1016/S0040-4039(96)02251-4 Get rights and content

Abstract

Limonene (1) was converted in one step into two diasteroisomers 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.

The title compound has been obtained in one step from limonene under the hydroformylation conditions employing PtCl₂L₂/PPh₃/SnCl₂ systems as catalysts (L= PPh₃, L₂ = 1,3-bis(diphenylphosphino)propane; 1,4-bis (diphenylphosphino)butane).

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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

Abstract

J. Mol. Catal.

J. Organometall. Chem.

J. Organomet. Chem.