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Asymmetric Synthesis of Spirocyclic β‐Lactams via Copper‐Catalyzed Kinugasa/Michael Domino Reactions

Abstract
The first copper‐catalyzed highly chemo‐, regio‐, diastereo‐, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne‐tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β‐lactams possessing four contiguous stereocenters, including one quaternary and one tetra‐substituted stereocenter.
Main Authors
Shu, Tao Zhao, Long Li, Sun Chen, Xiang-Yu von Essen, Carolina Rissanen, Kari Enders, Dieter
Format
Articles Research article
Published
2018
Series
Angewandte Chemie
Subjects
asymmetric synthesis
Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/28156531
Publisher
Wiley
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-201808143826Use this for linking
Review status
Peer reviewed
ISSN
1433-7851
DOI
https://doi.org/10.1002/ange.201806931
Language
English
Published in
Angewandte Chemie
Citation
  • Shu, T., Zhao, L., Li, S., Chen, X.-Y., von Essen, C., Rissanen, K., & Enders, D. (2018). Asymmetric Synthesis of Spirocyclic β‐Lactams via Copper‐Catalyzed Kinugasa/Michael Domino Reactions. Angewandte Chemie, 130(34), 11151-11154. https://doi.org/10.1002/ange.201806931
License
In CopyrightOpen Access
Copyright© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA

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