Copper and iridium conjugate addition – cyclisation processes; domino reactions
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Solana González2015.docx (8.199Mb)
Date
30/06/2015Author
Solana González, Jorge
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Abstract
Asymmetric conjugate addition of bis(pinacolato)diboron followed by aldol cyclisation of
enone diones under the action of a chiral copper catalyst has been developed.This
enantioselective process, using a chiral bisphosphine as ligand, allows the formation of
bicyclic alcohols with four contiguous stereocentres in high diastero- and enantioselectivity.
This catalytic system has been applied to the parallel kinetic resolution of a racemic β-
ketoamide. Further functionalization of the bicyclic alcohols synthesised was also possible. A domino addition of arylboronic acids and cyclisation of alkynones via an undescribed
iridium 1-4-migration process has been developed. A range of tricyclic compounds using a
variety of arylboronic acids have been synthesised in good yields and high
diasteroselectivity. The use of chiral bisphosphine ligand together with an iridium salt allows
the formation of enantioenriched compounds in moderate yield.
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