Download chiral primary, secondary and tertiary amines as organocatalysts in

Survey
yes no Was this document useful for you?
   Thank you for your participation!

* Your assessment is very important for improving the work of artificial intelligence, which forms the content of this project

Transcript
CHIRAL PRIMARY, SECONDARY AND TERTIARY AMINES AS
ORGANOCATALYSTS IN ASYMMETRIC CASCADE REACTIONS
Dr. Carlos Arróniz
The field of organocatalysis has evolved rapidly in the last decade and the use of chiral
amines as catalysts has become a powerful strategy in stereoselective synthesis. The
seminar will present asymmetric multi-step reactions promoted by chiral amines. The
first part of the talk will focus on the ability of primary amino alcohols to perform a
domino Michael-aldol reaction via iminium and enamine activation.1 The seminar will
then move on to the cooperative catalysis between chiral amines and transition metals
in multicatalytic cascades sequences. In particular, this second part will be centred on
the combination of iminium, enamine and Lewis acid catalysis for a carbocyclization of
aldehydes with alkynes;2 and on the combination of ammonium and Lewis acid
catalysis for a formal [3+2] cycloaddition reaction.3
Multicatalytic Cascade Sequences
Org. Biomol. Chem. 2011, 9, 5079–5085.
2
Chem. Eur. J. 2010, 16, 1750–1753.
3
Eur. J. Org. Chem. 2011, 3755–3760.