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Ligand bite angle-dependent palladium-catalyzed cyclization of propargylic carbonates to 2-alkynyl azacycles or cyclic dienamides.

Abstract:
The regioselectivity of the palladium-catalyzed cyclization of propargylic carbonates with sulfonamide nucleophiles is critically dependent on the bite angle of the bidentate phosphine ligand. Ligands with small bite angles favor attack on the central carbon atom of an allenylpalladium intermediate to afford cyclic dienamide products, whereas the use of those with large bite angles leads to alkynyl azacycles, with high stereoselectivity. A computational analysis of the reaction pathway is also presented.
Publication status:
Published

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Publisher copy:
10.1002/anie.201309162

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Inorganic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Angewandte Chemie (International ed. in English)
Volume:
53
Issue:
7
Pages:
1915-1920
Publication date:
2014-02-05
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
URN:
uuid:160ac668-3d81-4fbd-a98e-beb688b533b6
Source identifiers:
447889
Local pid:
pubs:447889

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