124685-70-7Relevant articles and documents
Photolytic reactions of chromium aminocarbene complexes. Conversion of amides to α-amino acids
Hegedus, Louis S.,Schwindt, Mark A.,De Lombaert, Stéphane,Imwinkelried, Rene
, p. 2264 - 2273 (2007/10/02)
A variety of tertiary amides was converted to chromium aminocarbene complexes by reaction with Na2Cr(CO)5 and trimethylsilyl chloride. Photolysis of these carbene complexes in methanol or tert-butyl alcohol solvent produced α-amino esters in good to excellent yield. Aminocarbene complexes containing chiral oxazolidine groups were synthesized and photolyzed in alcohol to produce chiral α-amino esters in 50-93% de. Pentacarbonyl[(dibenzylamino)(methyl)carbene]chromium(0) was prepared in high yield by the N-benzylation of the corresponding monobenzyl amino complex. Base-assisted alkylation of the methyl group with a variety of halides followed by photolysis in methanol produced the alkylated alanine methyl ester in excellent overall yield. Other aminocarbene complexes underwent similar reactions. With chiral, optically active aminocarbene complexes, the alkylated alanine derivative was produced with high diastereoselectivity.