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Sulfone mediated cyclobutanone to alpha alkoxycyclopentanone ring expansion reactions scope limitations and applications



Sulfone mediated cyclobutanone to alpha alkoxycyclopentanone ring expansion reactions scope limitations and applications



Tetrahedron 46(13-14): 4925-4950



The bicycloalkanones (1)-(3) were treated with the lithiated sulphone (4) to give the ring expanded .alpha.-methoxyketones (12), (14) and (16) generally as a mixture of epimers. The same bicycloalkanones furnished the .alpha.-benzyloxyketones (13), (15) and (17) on reaction with reagent (5). The ketone (3) reacted with the sulphone anion (6) to give, after Lewis acid treatment, the .alpha.-allyloxycyclopentanone derivatives (27a) and (27b) and one of these compounds (27b) was transformed into the ether (31). The bicycloheptanone (20) was converted into four ring-expanded products (22a), (22b), (24a) and (24b) and one of the compounds (24a) was used to synthesise the prostacyclin analogue (36). A brief study was made of the mechanism of the Lewis-acid catalysed rearrangement of the intermediate hydroxy sulphone to the ring-expanded compounds.

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