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Highly enantioselective [5 + 2] annulations through cooperative N-heterocyclic carbene (NHC) organocatalysis and palladium catalysis

Singha, Santanu, Patra, Tuhin, Daniliuc, Constantin G. and Glorius, Frank 2018. Highly enantioselective [5 + 2] annulations through cooperative N-heterocyclic carbene (NHC) organocatalysis and palladium catalysis. Journal of the American Chemical Society 140 (10) , pp. 3551-3554. 10.1021/jacs.8b00868

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Abstract

The highly enantioselective [5 + 2] annulation of enals with vinylethylene carbonates through a cooperative N-heterocyclic carbene (NHC)/Pd catalytic system is reported. The use of a bidentate phosphine ligand was crucial to prevent coordination of the NHC organocatalyst to the active Pd catalyst. The complementary and matched combination of the chiral NHC catalyst and chiral phosphine ligand promotes high levels of both reactivity and enantioselectivity (mostly ≥99% ee).

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Last Modified: 18 Feb 2021 15:30
URI: http://orca.cardiff.ac.uk/id/eprint/138433

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