220715-08-2Relevant academic research and scientific papers
Stereocontrol in the intramolecular Buchner reaction of diazoamides and diazoesters
Moody, Christopher J.,Miah, Soyfur,Slawin, Alexandra M. Z.,Mansfield, Darren J.,Richards, Ian C.
, p. 4067 - 4075 (2007/10/03)
Dirhodium(II) catalysed decomposition of diazoamide 5 resulted in formation of β-lactams 6/7 by intramolecular C-H insertion, the intramolecular Buchner reaction being disfavoured for conformational reasons. The diazoamide 8, however, gave products resulting from both the intramolecular Buchner reaction and C-H insertion. Chiral diazoesters 14-16 derived from α-substituted benzyl alcohols gave cycloheptatrienes in a highly diastereoselective manner; the norcaradiene isomer of the cycloheptatrienes was readily intercepted in a Diels-Alder reaction with 4-phenyl-1,2,4-triazoline-3,5-dione to give adducts 19-21.
