The Paternò-Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6-oxabicyclo[3.2.0]heptan-1-ol. The bicyclic structure underwent selective reductive ring opening and acid-catalyzed pinacol-type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism-dependent diastereoselectivity

Stereoselective and regioselective pinacol-type rearrangement of a fused bicyclic oxetanol scaffold

Nicola Melis
Primo
Membro del Collaboration Group
;
Alberto Luridiana
Secondo
Membro del Collaboration Group
;
Francesco Secci
Membro del Collaboration Group
;
Angelo Frongia
Membro del Collaboration Group
;
2017-01-01

Abstract

The Paternò-Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6-oxabicyclo[3.2.0]heptan-1-ol. The bicyclic structure underwent selective reductive ring opening and acid-catalyzed pinacol-type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism-dependent diastereoselectivity
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/234134
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