Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters. A versatile preparation of diastereomeric monoterpenoids: (±)-fragranol and (±)-grandisol

Mixtures of ( E and Z)-2-cyclobutylidenepropyl sulfonates, readily available from α,α-disubstituted cyclobutanones arising from suitable cyclopropane derivatives ring expansion, underwent regioselective and stereospecific reduction by formate anion to offer, through π-1,1-trimethyleneallylpalladium...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2003-11, Vol.59 (47), p.9433-9440
Main Authors: Bernard, Angela M, Frongia, Angelo, Secci, Francesco, Delogu, Giovanna, Ollivier, Jean, Piras, Pier P, Salaün, Jacques
Format: Article
Language:English
Subjects:
cyclobutanes
natural products
palladium and compounds
stereospecificity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Mixtures of ( E and Z)-2-cyclobutylidenepropyl sulfonates, readily available from α,α-disubstituted cyclobutanones arising from suitable cyclopropane derivatives ring expansion, underwent regioselective and stereospecific reduction by formate anion to offer, through π-1,1-trimethyleneallylpalladium complexes formed upon treatment with palladium(0), a new and convenient entry to the diastereomeric four-membered ring monoterpenoids (±)-fragranol and (±)-grandisol. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.09.074