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

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.

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 Creators:
Müller, Steffen1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: electrocyclic reactions; enantioselective organocatalysis; heterocycles; diastereoselectivity; 2-pyrazolines
 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.

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Language(s): eng - English
 Dates: 2010-04-292010-05-202010-07-01
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-0029-1218792
 Degree: -

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Title: Synthesis
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: (13) Sequence Number: - Start / End Page: 2171 - 2178 Identifier: ISSN: 0039-7881
CoNE: https://pure.mpg.de/cone/journals/resource/954925448757