756845-41-7Relevant academic research and scientific papers
Enantiomerically pure polyheterocyclic spiro-β-lactams from trans-4-hydroxy-l-proline
Cremonesi, Giuseppe,Croce, Piero Dalla,Fontana, Francesco,La Rosa, Concetta
experimental part, p. 2010 - 2017 (2010/06/16)
"Chemical Equation Presented" The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidin
Novel asymmetric approach to proline-derived spiro-β-lactams
Khasanov, Alisher B.,Ramirez-Weinhouse, Michele M.,Webb, Thomas R.,Thiruvazhi, Mohan
, p. 5766 - 5769 (2007/10/03)
We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-β-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudinger chemistry and later is sacrificed to obtain optically active 5.4-spiro-β-lactams. The scope, limitations, and mechanistic rationale for the observed results of Staudinger Chemistry of the acid chloride of 4-alkyl(aryl)sulfonyloxy-L-proline with imines are also discussed.
