1562809-94-2Relevant academic research and scientific papers
Convergent access to polycyclic cyclopentanoids from α,β- unsaturated acid chlorides and alkynes through a reductive coupling, nazarov cyclization sequence
Chaplin, Jason H.,Jackson, Kristal,White, Jonathan M.,Flynn, Bernard L.
, p. 3659 - 3664 (2014)
Reductive coupling of α,β-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, α-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids.
