Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines.
The phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactions, run under very mild conditions, for the preparation of highly functionalized tetrahydropyridines in yields of up to 98% and trans/cis ratios of up to 97:3. In addition to steps that are typical of nucleophilic phosphine-catalyzed reactions of allenoates, the mechanism of this new reaction features apparent nucleophilic aromatic substitution and concomitant desulfonylation, processes hitherto unknown during phosphine-promoted cycloaddition reactions. Notably, these reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphine-catalyzed transformations.
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Hongchao
H
Guo
Qihai
Q
Xu
Ohyun
O
Kwon
D000466:Alkadienes / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D010720:Phosphines / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis*
D000466:Alkadienes; D001388:Aziridines; D002264:Carboxylic Acids; D010720:Phosphines; D011725:Pyridines; C025947:propadiene; C044646:phosphine