Beilstein J. Org. Chem.2013,9, 1443–1447, doi:10.3762/bjoc.9.163
Petersonelimination. The approach allows functionalised cyclopentanols containing two vicinal quaternary stereocentres to be conveniently prepared from simple starting materials.
Keywords: cyclisation; free radical; Petersonelimination; reduction; samarium; telescoped process; Introduction
Samarium
” individual steps: spirocyclisation, lactone reduction and Petersonelimination allow rapid access to functionalised cyclopentanols, containing two vicinal quaternary stereocentres, from simple starting materials. The sequence involves the use of two activated SmI2 reagent systems, and a silicon stereocontrol
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Telescoped spirocyclisation/lactone reduction/Petersonelimination
With an efficient process combining spirocyclisation and lactone reduction in hand, we proposed that manipulation of the triol products by Petersonelimination [43][44] could be added to the telescoped sequence. Crucially, Peterson
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Graphical Abstract
Scheme 1:
SmI2-mediated cyclisations directed by a C–Si bond.