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Palladium(0)-Catalyzed Asymmetric Synthesis of 1,2,3,4-Tetrahydro-2-vinylquinoxalines (1999)

Massacret, Magali ; Lhoste, Paul ; Sinou, Denis

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 129-134

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ISSN: 1434-193X

Keywords: Tetrahydro-2-vinylquinoxaline ; Cyclization ; Palladium ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -Reaction of (Z)-1,2-bis(methoxycarbonyloxy)but-2-ene (2) with various N,N-bis(arylsulfonyl)-o-phenylenediamines 1 was catalyzed by a palladium complex associated with chiral ligands to give optically active 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydro-2-vinylquinoxalines 3 with up to 62% ee. The use of (S)-MeOBIPHEP as the chiral ligand and N,N-bis(p-tolylsulfonyl)-o-phenylenediamine (1i) as the nucleophile led to the highest ee at 25 °C, regardless of the solvent used. The enantioselectivity of the cyclization is strongly affected by the nature of the substituents at the nitrogen atom.

Additional Material: 4 Tab.

Type of Medium: Electronic Resource

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