Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines
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Peer-reviewed
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Article
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Authors
Poh, J-S
Makai, S
von Keutz, T
Tran, DN
Abstract
We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10-20 minutes with high enantioselectivity (89-98 % de/ee), moderate yields and a wide functional group tolerance.
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Keywords
allenes, asymmetric catalysis, copper, diazo compounds, flow chemistry
Journal Title
Angewandte Chemie International Edition (English)
Conference Name
Journal ISSN
1433-7851
1521-3773
1521-3773
Volume Title
56
Publisher
Wiley
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
We are grateful to the Cambridge Home and European Scholarship Scheme (J.S.P.), Erasmus Scholarship Scheme (T.v.K. and S.M.), Swiss National Science Foundation (D.N.T.), UCB Biopharma SPRL (J.S.P. and P.P.) and EPSRC (C.B. and S.V.L., grant no. EP/K009494/1, EP/K039520/1 and EP/M004120/1) for financial support.