English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Catalytic Asymmetric 6π-Electrocyclization: Accessing Highly Substituted Optically Active 2-Pyrazolines via Diastereoselective Alkylations

MPS-Authors
/persons/resource/persons58836

Müller,  Steffen
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;

Locator
There are no locators available
Fulltext (public)
There are no public fulltexts available
Supplementary Material (public)
There is no public supplementary material available
Citation

Müller, S., & List, B. (2010). Catalytic Asymmetric 6π-Electrocyclization: Accessing Highly Substituted Optically Active 2-Pyrazolines via Diastereoselective Alkylations. Synthesis, (13), 2171-2178. doi:10.1055/s-0029-1218792.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-8E07-8
Abstract
The chiral phosphoric acid catalyzed asymmetric electrocyclization of α,β-unsaturated hydrazones has been studied. This reaction is one of the first catalytic asymmetric 6π-electrocyclizations reported, and enables the synthesis of 2-pyrazolines in high yields and enantiomeric ratios. The obtained products are not only interesting because of their pharmaceutical properties, but can be manipulated in highly diastereoselective fashion, as shown for alkylation reactions. Thus, the combination of catalytic asymmetric 6π-electrocyclization followed by diastereoselective alkylation can provide interesting synthetic building blocks in optically active form.