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

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 PtCl 2(PPh 3) 2/PPh 3/SnCl 2 and PtCl 2(diphosphine)/PPh 3 /SnCl 2 systems as bifunctional catalysts whose diphosphines were 1,3-bis(diphenylphosphino)prop...

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Bibliographic Details
Published in:Tetrahedron letters 1997, Vol.38 (1), p.41-44
Main Authors: Dias, Adelson de O., Augusti, Rodinei, dos Santos, Eduardo N., Gusevskaya, Elena V.
Format: Article
Language:English
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Summary: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 PtCl 2(PPh 3) 2/PPh 3/SnCl 2 and PtCl 2(diphosphine)/PPh 3 /SnCl 2 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 PtCl 2(dppb)/PPh 3 /SnCl 2 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 PtCl 2L 2/PPh 3/SnCl 2 systems as catalysts (L= PPh 3, L 2 = 1,3-bis(diphenylphosphino)propane; 1,4-bis (diphenylphosphino)butane).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02251-4