One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; Functionalisation to homoallylic boronate carboxylate ester derivatives
The β-borylation reaction of α,β-unsaturated aldehyde-derived imines, formed in situ, has been studied using a one-pot methodology, as a route to β-boryl aldehydes. The instability of the β-boryl aldehydes meant that derivatisation was required and routes
Pujol, Alba,Calow, Adam D. J.,Batsanov, Andrei S.,Whiting, Andrew
p. 5122 - 5130
(2015/05/13)
Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach
We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from α,β-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated β-borylation/transimination/reduction/oxidation) followed by the specific ether group formation which deliver the desired products (R)-fluoxetine in 45% yield (96% ee) and (S)-duloxetine in 47% yield (94% ee). This journal is the Partner Organisations 2014.
Calow, Adam D. J.,Fernandez, Elena,Whiting, Andrew
p. 6121 - 6127
(2014/08/05)
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