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Palladium(0)‐Catalyzed Asymmetric Synthesis of 1,2,3,4‐Tetrahydro‐2‐vinylquinoxalines
Author(s) -
Massacret Magali,
Lhoste Paul,
Sinou Denis
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199901)1999:1<129::aid-ejoc129>3.0.co;2-6
Subject(s) - chemistry , palladium , catalysis , nitrogen atom , nucleophile , ligand (biochemistry) , medicinal chemistry , optically active , enantioselective synthesis , solvent , stereochemistry , organic chemistry , receptor , ring (chemistry) , biochemistry
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.