University of Cagliari
Stereoselective and regioselective pinacol-type rearrangement of a fused bicyclic oxetanol scaffold
Nicola MelisFirst
Member of the Collaboration Group
;Alberto LuridianaSecond
Member of the Collaboration Group
;Francesco SecciMember of the Collaboration Group
;Angelo FrongiaMember of the 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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