Intramolecular photoaddition of vinylogous amides with allenes: a novel approach to the synthesis of pyrroles.
Irradiation of vinylogous amide or imide 5 (R = H, alkyl, or Ac) leads to the selective formation of either crossed photoadduct 7 (R = Ac) or parallel photoadduct 8 (R = H or alkyl) as a function of the nature of the group R. The latter result leads to a novel approach to the synthesis of pyrroles, that is, 8'.
Winkler
Jeffrey D
JD
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA. winkler@sas.upenn.edu
Ragains
Justin R
JR
D000466:Alkadienes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*
D000466:Alkadienes; D000577:Amides; D011758:Pyrroles; C025947:propadiene