English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans

MPS-Authors
/persons/resource/persons200419

Lee,  Sunggi
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons199547

Bae,  Han Yong
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)

Lee, Bae, List 2018.pdf
(Postprint), 676KB

Supplementary Material (public)
There is no public supplementary material available
Citation

Lee, S., Bae, H. Y., & List, B. (2018). Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans. Angewandte Chemie International Edition, 57(37), 12162-12166. doi:10.1002/anie.201806312.


Cite as: https://hdl.handle.net/21.11116/0000-0002-16A3-D
Abstract
O‐heterocycles bearing tetrasubstituted stereogenic centers are prepared via catalytic chemo‐ and enantioselective nucleophilic additions to ketoaldehydes, in which the ketone reacts preferentially over the aldehyde. Five‐ and six‐membered rings with both aromatic and aliphatic substituents, as well as an alkynyl substituent, are obtained. Moreover, 2,2,5‐trisubstituted and 2,2,5,5‐tetrasubstituted tetrahydrofurans are synthesized with excellent stereoselectivities. Additionally, the synthetic utility of the described method is demonstrated with a three‐step synthesis of the side chain of anhydroharringtonine.