Stereospecific cleavage of carbon-phosphorus bonds: stereochemical course of the phosphinoyl curtius (Harger) reaction |
| |
Authors: | Denmark Scott E Dorow Roberta L |
| |
Institution: | Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. |
| |
Abstract: | The homochiral phosphinic azides (R,R)-1 and (S,S)-1 were prepared in enantiomerically pure form by resolution of diastereomeric phosphinamides derived from (S)-l-phenylethylamine and (R)-phenylglycine. Irradiation of the azides in methanol induced a photo-Curtius rearrangement to phosphonamidates in which the stereogenic carbon unit migrated to a nitrogen atom. Hydrolysis of the phosphonamidates produced 1-phenylethylamine, which was 99.0% e.e. and of the same configuration as the carbon unit in the starting azide (99.0% retention). |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|